Organic electroluminescent element, light-emitting material therefor, light emitting device, display device, and illumination device

ABSTRACT

An organic electroluminescent element including a luminescent compound represented by the following formula (in which R 1  to R 14  each independently represent a hydrogen atom, a deuterium atom, an alkyl group, an aryl group, a heteroaryl group, a fluorine atom, a cyano group, an amino group, an alkoxy group, an aryloxy group, a thio group, or a silyl group, and 8 to 13 groups out of R 1  to R 14  each represent a hydrogen atom or a deuterium atom.) in a light emitting layer has high durability and excellent chromaticity.

TECHNICAL FIELD

The present invention relates to an organic electroluminescent elementand a light emitting material for an organic electroluminescent elementfor use in the element. The present invention further relates to a lightemitting device, a display device, or an illumination device each usingthe organic electroluminescent element.

BACKGROUND ART

Since organic electroluminescent elements (which may hereinafter also bereferred to as “elements” or “organic EL elements”) are capable ofhigh-luminance light emitting with driving at a low voltage, they havebeen actively researched and developed. The organic electroluminescentelements have organic layers between a pair of electrodes, and utilize,for light emitting, energy of the exciton generated as a result ofrecombination of electrons injected from a cathode and holes injectedfrom an anode in the organic layer. Since the organic electroluminescentelements are capable of being provided as an element having variouslight emitting wavelengths, have a high response speed, and arerelatively thin and light-weight, it is expected that the element can beemployed in a wide range of applications. Above all, it is important todevelop an organic electroluminescent element having high blue colorpurity and luminous efficiency in applications with full-color displays,and the like, and the outcomes of various research and developmentstudies up to now have been reported.

For example, PTL 1 describes a blue fluorescent light emitting materialhaving a diaminopyrene skeleton containing two substituted orunsubstituted amino groups, and also describes that an organicelectroluminescent device having excellent blue color purity andluminous efficiency can be provided. However, a compound having anextended π conjugation system of a pyrene skeleton has substantially notbeen investigated in the prior art and PTL 1 has neither disclosure norsuggestion of extension of the π conjugation system of a pyreneskeleton.

Meanwhile, PTL 2 discloses an organic electroluminescent element havinga strong luminous intensity and high durability, using a material havingtwo fused rings formed in a tetracene skeleton, and the literaturedescribes a dibenzopyrene skeleton as an example of the skeleton.However, the same literature does not substantially mention adibenzopyrene skeleton, and has neither disclosure nor suggestion ofspecific exemplary compounds having dibenzopyrene skeletons.

PTL 3 describes the use of a compound of a dibenzopyrene skeleton(liquid crystal material) as a host material in a light emitting layerof a phosphorescent organic electroluminescent element, and furtherdescribes that an organic electroluminescent element having highluminance and high efficiency is obtained. However, the same literatureonly describes the use of the compound as a host material of alightemitting layer, and has neither disclosure nor suggestion of the use ofa compound having a dibenzopyrene skeleton as a light emitting materialin a light emitting layer.

On the other hand, in some instances, compounds having dibenzopyreneskeletons are used in other fields, and for example, PTL 4 describes anorganic transistor including a compound having a dibenzopyrene skeleton(dibenzotetracene skeleton). However, the same literature does notmention the presence or absence of luminous function, the luminousintensity, or the chromaticity when a compound having a dibenzopyreneskeleton is used in an organic electroluminescent element.

CITATION LIST Patent Literature

-   [PTL 1] JP-A-2004-204238-   [PTL 2] JP-A-05-2143334-   [PTL 3] JP-A-2005-82702-   [PTL 4] JP-A-2008-124094

SUMMARY OF INVENTION Technical Problem

However, according to the investigation conducted by the presentinventors, it could be seen that the blue fluorescent light emittingmaterial having a diaminopyrene skeleton described in PTL 1 has a peakwavelength for light emission on the long wave side and is notsatisfactory in the blue color purity. Although an unsubstituteddibenzopyrene is described as an exemplary compound in PTL 2, it couldalso be seen that the compound has strong association, leading toassociative light emission and thus poor chromaticity, and therefore, itis inappropriate as a light emitting material. It could be seen that thecompound having a dibenzopyrene skeleton (liquid crystal material)described in PTL 3 has poor heat resistance as the compound, and whenthe compound is used as a light emitting material of an organicelectroluminescent element, it has low luminous efficiency.

The present invention aims to solve the foregoing problems. It is anobject of the present invention to provide a light emitting material foran organic electroluminescent element, having high heat resistance andexcellent chromaticity, and an organic electroluminescent element havinghigh luminous efficiency and excellent chromaticity, using the lightemitting material.

Solution to Problem

Therefore, the present inventors have conducted intensive investigationsfor the purpose of providing a light emitting material for an organicelectroluminescent element, having high heat resistance and excellentchromaticity, and an organic electroluminescent element having highluminous efficiency and excellent chromaticity, using the light emittingmaterial. As a result, they have found that the above-described problemscan be solved by using a compound having a specific structure, therebyproviding the present invention as described below.

[1] An organic electroluminescent element including a substrate, a pairof electrodes including an anode and a cathode, disposed on thesubstrate, and at least one organic layer including a light emittinglayer, disposed between the electrodes,

in which the light emitting layer contains a luminescent compoundrepresented by the following general formula (1).

(In the formula, R¹ to R¹⁴ each independently represent a hydrogen atom,a deuterium atom, an alkyl group, an aryl group, a heteroaryl group, afluorine atom, a cyano group, an amino group, an alkoxy group, anaryloxy group, a thio group, or a silyl group, and these may be bondedto each other to form a ring. However, 8 to 13 groups out of R¹ to R¹⁴each represent a hydrogen atom or a deuterium atom.)

[2] In the organic electroluminescent element as described in [1], atleast one of R¹ to R¹⁴ in the general formula (1) is preferably anelectron donating substituent.

[3] In the organic electroluminescent element as described in [1] or[2], at least one of R¹ to R¹⁴ in the general formula (1) is preferablyan amino group.

[4] In the organic electroluminescent element as described in any one of[1] to [3], the luminescent compound represented by the general formula(1) is preferably a luminescent compound represented by the followinggeneral formula (2).

(In the formula, R² to R²⁴ each independently represent a hydrogen atom,a deuterium atom, an alkyl group, an aryl group, a heteroaryl group, afluorine atom, a cyano group, an amino group, an alkoxy group, anaryloxy group, a thio group, or a silyl group, and these may be bondedto each other to form a ring. R¹⁵ and R¹⁶ each independently representan alkyl group, an aryl group, a heteroaryl group, or a hydrogen atom,and may be bonded to each other to form a ring or may be bonded to R² orR¹⁴ to form a ring.)

[5] In the organic electroluminescent element as described in any one of[1] to [3], the luminescent compound represented by the general formula(1) is preferably a luminescent compound represented by the followinggeneral formula (3).

(In the formula, R¹ and R⁴ to R¹⁴ each independently represent ahydrogen atom, a deuterium atom, an alkyl group, an aryl group, aheteroaryl group, a fluorine atom, a cyano group, an amino group, analkoxy group, an aryloxy group, a thio group, or a silyl group, andthese may be bonded to each other to form a ring. R³¹ to R³³ eachindependently represent an alkyl group, an aryl group, a heteroarylgroup, or a hydrogen atom, and R³² and R³³ may be bonded to each otherto form a ring.)

[6] In the organic electroluminescent element as described in any one of[1] to [3], the luminescent compound represented by the general formula(1) is preferably a luminescent compound represented by the followinggeneral formula (4).

(In the formula, R¹, R⁴ to R⁸ and R¹¹ to R¹⁴ each independentlyrepresent a hydrogen atom, a deuterium atom, an alkyl group, an arylgroup, a heteroaryl group, a fluorine atom, a cyano group, an aminogroup, an alkoxy group, an aryloxy group, a thio group, or a silylgroup, and these may be bonded to each other to form a ring. R³¹ to R³⁶each independently represent an alkyl group, an aryl group, a heteroarylgroup, or a hydrogen atom, R³² and R³³ may be bonded to each other toform a ring, and R³⁵ and R³⁶ may be bonded to each other to form aring.)

[7] In the organic electroluminescent element as described in any one of[1] to [3], the luminescent compound represented by the general formula(1) is preferably a luminescent compound represented by the followinggeneral formula (5).

(In the formula, R² to R⁷ and R⁹ to R¹⁴ each independently represent ahydrogen atom, a deuterium atom, an alkyl group, an aryl group, aheteroaryl group, a fluorine atom, a cyano group, an amino group, analkoxy group, an aryloxy group, a thio group, or a silyl group, andthese may be bonded to each other to form a ring. R¹⁷ to R²⁰ eachindependently represent an alkyl group, an aryl group, a heteroarylgroup, or a hydrogen atom, and R¹⁷ and R¹⁹ may be bonded to any of R²,R¹⁴, or R¹⁸ and any of R⁷, R⁹, or R²⁰, respectively, to form a ring.)

[8] In the organic electroluminescent element as described in any one of[1] to [3], the luminescent compound represented by the general formula(1) is preferably a luminescent compound represented by the followinggeneral formula (6).

(In the formula, R² to R⁹ and R¹¹ to R²⁴ each independently represent ahydrogen atom, a deuterium atom, an alkyl group, an aryl group, aheteroaryl group, a fluorine atom, a cyano group, an amino group, analkoxy group, an aryloxy group, a thio group, or a silyl group, andthese may be bonded to each other to form a ring. R²¹ to R²⁴ eachindependently represent alkyl group, an aryl group, a heteroaryl group,or a hydrogen atom, and R²¹ and R²³ may be bonded to any of R², R¹⁴, orR²² and any of R⁹, R¹¹, or R²⁴, respectively, to form a ring.)

[9] In the organic electroluminescent element as described in any one of[1] to [3], the luminescent compound represented by the general formula(1) is preferably a luminescent compound represented by the followinggeneral formula (7).

(In the formula, R² and R⁴ to R¹⁴ each independently represent ahydrogen atom, a deuterium atom, an alkyl group, an aryl group, aheteroaryl group, a fluorine atom, a cyano group, an amino group, analkoxy group, an aryloxy group, a thio group, or a silyl group, andthese may be bonded to each other to form a ring. R²⁵ to R²⁸ eachindependently represent an alkyl group, an aryl group, a heteroarylgroup, or a hydrogen atom, and R²⁵ and R²⁷ may be bonded to any of R²,R¹⁴, or R²⁶ and any of R², R⁴, or R²⁸, respectively, to form a ring.)

[10] In the organic electroluminescent element as described in any oneof [1] to [9], the light emitting layer preferably contains ananthracene-based host material.

[11] In the organic electroluminescent element as described in any oneof [1] to [10], the light emitting layer is preferably formed by avacuum deposition process.

[12] In the organic electroluminescent element as described in any oneof [1] to [10], the light emitting layer is preferably formed by a wetprocess.

[13] A light emitting device using the organic electroluminescentelement as described in any one of [1] to [12].

[14] A display device using the organic electroluminescent element asdescribed in any one of [1] to [12].

[15] An illumination device using the organic electroluminescent elementas described in any one of [1] to [12].

[16] A light emitting material for an organic electroluminescentelement, represented by the following general formula (1).

(In the formula, R¹ to R¹⁴ each independently represent a hydrogen atom,a deuterium atom, an alkyl group, an aryl group, a heteroaryl group, afluorine atom, a cyano group, an amino group, an alkoxy group, anaryloxy group, a thio group, or a silyl group, and these may be bondedto each other to form a ring. However, 8 to 13 groups out of R¹ to R¹⁴each represent a hydrogen atom or a deuterium atom.)

Advantageous Effects of Invention

The organic electroluminescent element of the present invention has highluminous efficiency and excellent chromaticity. Further, the lightemitting material for an organic electroluminescent element of thepresent invention has high heat resistance and excellent chromaticity,and accordingly, such an excellent organic electroluminescent elementcan be easily prepared. Further, the light emitting device, the displaydevice, and the illumination device of the present invention haveadvantageous effects in that the power consumption is low and the bluecolor purity is excellent.

BRIEF DESCRIPTION OF DRAWINGS

FIG. 1 is a schematic view showing one example of a configuration of anorganic electroluminescent element according to the present invention.

FIG. 2 is a schematic view showing one example of alight emitting deviceaccording to the present invention.

FIG. 3 is a schematic view showing one example of an illumination deviceaccording to the present invention.

DESCRIPTION OF EMBODIMENTS

Hereinafter, the disclosure of the present invention will be describedin detail. The description of the requirements of the configuration asdescribed below is based on representative embodiments and specificexamples of the present invention, but the present invention is notlimited to these embodiments and specific examples. Incidentally, in thepresent specification, the numerical value range expressed with “to”means a range including the numerical values before and after “to” asthe lower limit and the upper limit, respectively.

[Organic Electroluminescent Element and Light Emitting Material forOrganic Electroluminescent Element, Represented by General Formula (1)]

The light emitting material for an organic electroluminescent element ofthe present invention may be represented by the following generalformula (1).

Furthermore, the organic electroluminescent element of the presentinvention includes a substrate, a pair of electrodes including an anodeand a cathode, disposed on the substrate, and at least one organic layerincluding a light emitting layer, disposed between the electrodes, inwhich the light emitting layer contains a luminescent compoundrepresented by the following general formula (1).

(In the formula, R¹ to R¹⁴ each independently represent a hydrogen atom,a deuterium atom, an alkyl group, an aryl group, a heteroaryl group, afluorine atom, a cyano group, an amino group, an alkoxy group, anaryloxy group, a thio group, or a silyl group, and these may be bondedto each other to form a ring. However, 8 to 13 groups out of R¹ to R¹⁴each represent a hydrogen atom or a deuterium atom.)

That is, the organic electroluminescent element of the present inventionmay contain the light emitting material for an organicelectroluminescent element of the present invention, which may berepresented by the general formula (1), as a luminescent compound in thelight emitting layer.

Hereinafter, other configurations of the luminescent compoundrepresented by the general formula (1), which is the light emittingmaterial for an organic electroluminescent element of the presentinvention, and the organic electroluminescent element of the presentinvention will be described in detail.

In the present invention, the hydrogen atom which is used withoutparticular distinction at each occurrence in the description of therespective general formulae also includes isotopes (a deuterium atom andthe like), and the atoms additionally constituting the substituent arealso intended to include isotopes of the atoms.

In the present invention, the “substituent” at each occurrence may befurther substituted with a substituent. For example, the “alkyl group”at each occurrence in the present invention includes an alkyl groupsubstituted with a fluorine atom (for example, a trifluoromethyl group),an alkyl group substituted with an aryl group (for example, atriphenylmethyl group), and the like, but “an alkyl group having 1 to 6carbon atoms” represents one having 1 to 6 carbon atoms, as any groupalso including substituted groups thereof.

The organic electroluminescent element of the present invention isexcellent in terms of luminous efficiency and color purity when thelight emitting layer contains the luminescent compound represented bythe general formula (1). The organic electroluminescent element of thepresent invention can have good blue color purity, as compared with thediaminopyrene compound described in JP-A-2004-204238, by shortening thelight emitting wavelength. Particularly, the luminescent compoundrepresented by the general formula (1) has a skeleton having an extendedbenzo-fused ring with respect to a pyrene skeleton, and thus despite itsextended conjugation π plane, it is an unexpected effect that the lightemitting wavelength is shortened and the blue color purity is improved.In this regard, the present invention has the inventive step withrespect to JP-A-2004-204238. The reason therefor is thought to be thatthe fused ring structure is extended in the direction perpendicular to atransition bipolar moment with respect to the pyrene skeleton and thedonating property of an amino group is reduced by twisting a substituenton the amino group.

On the other hand, the reason why the luminous spectrum is sharpened andthe blue color purity is thus improved in the luminescent compoundrepresented by the general formula (1) is not clear, but it is presumedto be that the change in the structures is small in the case oftransition from a ground state to an excited state in a centralskeleton, and when an electron donating group is used as a substituent,the central skeleton serves as an electron receiving group, therebyforming a donor and acceptor structure, and accordingly, the change inthe structures in the excited state becomes smaller.

In the general formula (1), 8 to 13 groups out of R¹ to R¹⁴ eachrepresent a hydrogen atom or a deuterium atom.

In the general formula (1), if the hydrogen atom in R¹ to R¹⁴ is atleast the lower limit of the range, the heat resistance of theluminescent compound represented by the general formula (1) is improved,and thus, the luminous efficiency of the element in the case of usingthe compound as a light emitting material in the light emitting layer ofthe organic electroluminescent element is increased. Not wishing to berestricted to any theory, the reason therefor is presumed that thecompound 35 used in Examples of JP-A-2005-82702 (corresponding to acompound having 6 hydrogen atoms in R¹ to R¹⁴ in the general formula(1)) exhibits a liquid crystal property, and accordingly, it has alowered melting point and the molecular motion increases, and thus, thethermal decomposition temperature becomes lowered.

On the other hand, the number of hydrogen atoms in R¹ to R¹⁴ in thegeneral formula (1) is no more than the above range, the chromaticity ofthe luminescent compound represented by the general formula (1) isimproved, and thus, when the compound is used as a light emittingmaterial in the light emitting layer of the organic electroluminescentelement, the chromaticity of the element is increased. Not wishing to berestricted to any theory, it is thought that as compared with anunsubstituted dibenzopyrene described in JP-A-05-214334, the associationamong the dibenzopyrene rings is inhibited by incorporating a specificsubstituent and the excimer light emission is thus inhibited, therebyobtaining these effects.

In the general formula (1), it is preferable that 10 to 12 groups of R¹to R¹⁴ each represent a hydrogen atom or a deuterium atom, and it ismore preferable that 10 groups of R¹ to R¹⁴ each represent a hydrogenatom or a deuterium atom. Further, in the case where R¹ to R¹⁴ eachrepresent a hydrogen atom or a deuterium atom, a hydrogen atom ispreferable to a deuterium atom.

In the general formula (1), R¹ to R¹⁴ each independently represent ahydrogen atom, a deuterium atom, an alkyl group, an aryl group, aheteroaryl group, a fluorine atom, a cyano group, an amino group, analkoxy group, an aryloxy group, a thio group, or a silyl group, andthese may be bonded to each other to form a ring.

It is preferable that each substituent other than the hydrogen atom andthe deuterium atom represented by R¹ to R¹⁴ be specifically thefollowing Substituent Group a.

<<Substituent Group a>>

An alkyl group (preferably having 1 to 30 carbon atoms, more preferablyhaving 1 to 20 carbon atoms, and particularly preferably having 1 to 10carbon atoms; for example, methyl, ethyl, isopropyl, t-butyl, n-octyl,n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, and cyclohexyl), an arylgroup (preferably having 6 to 30 carbon atoms, more preferably having 6to 20 carbon atoms, and particularly preferably having 6 to 12 carbonatoms; for example, phenyl, p-methylphenyl, naphthyl, and anthranyl), anamino group (the amino group may have a substituent, and the totalnumber of carbon atoms of the amino group including the substituent ispreferably from 0 to 30, more preferably from 0 to 20, and particularlypreferably from 0 to 10; the amino group is, for example, amino,methylamino, dimethylamino, diethylamino, dibenzylamino, diphenylamino,and ditolylamino), an alkoxy group (preferably having 1 to 30 carbonatoms, more preferably having 1 to 20 carbon atoms, and particularlypreferably having 1 to 10 carbon atoms; for example, methoxy, ethoxy,butoxy, and 2-ethylhexyloxy), and aryloxy group (preferably having 6 to30 carbon atoms, more preferably having 6 to 20 carbon atoms, andparticularly preferably having 6 to 12 carbon atoms; for example,phenyloxy, 1-naphthyloxy, and 2-naphthyloxy), an alkylthio group(preferably having 1 to 30 carbon atoms, more preferably having 1 to 20carbon atoms, and particularly preferably having 1 to 12 carbon atoms;for example, methylthio and ethylthio), an arylthio group (preferablyhaving 6 to 30 carbon atoms, more preferably having 6 to 20 carbonatoms, and particularly preferably having 6 to 12 carbon atoms; forexample, phenylthio), a heterocyclic thio group (preferably having 1 to30 carbon atoms, more preferably having 1 to 20 carbon atoms, andparticularly preferably having 1 to 12 carbon atoms; for example,pyridylthio, 2-benzoimizolylthio, 2-benzoxazolylthio, and2-benzothiazolylthio), a heterocyclic group (inclusive of an aromaticheterocyclic group, which preferably has 1 to 30 carbon atoms, and morepreferably 1 to 12 carbon atoms and in which examples of the hetero atominclude a nitrogen atom, an oxygen atom, a sulfur atom, a phosphorusatom, a silicon atom, a selenium atom, and a tellurium atom; andspecific examples thereof include pyridyl, pyrazinyl, pyrimidyl,pyridazinyl, pyrrolyl, pyrazolyl, triazolyl, imidazolyl, oxazolyl,triazolyl, isoxazolyl, isothiazolyl, quinolyl, furyl, thienyl,selenophenyl, tellurophenyl, piperidyl, piperidino, morpholino,pyrrolidyl, pyrrolidino, benzoxazolyl, benzoimidazolyl, benzothiazolyl,a carbazolyl group, an azepinyl group, and a silolyl group), and a silylgroup (the silyl group may have a substituent, and the total number ofcarbon atoms of the silyl group including the substituent is preferablyfrom 3 to 40, more preferably from 3 to 30, and particularly preferablyfrom 3 to 24; the silyl group is, for example, trimethylsilyl,triphenylsilyl, and phenyldimethylsilyl). These substituents may befurther substituted, and examples of the additional substituent includethe groups selected from the Substituent Group A as described below.Further, the substituent substituted with a substituent may be furthersubstituted, and examples of the additional substituent include thegroups selected from the Substituent Group A as described below. Inaddition, the substituent substituted with the substituent which hasbeen substituted with a substituent may be further substituted, andexamples of the additional substituent include the groups selected fromthe Substituent Group A as described below.

<<Substituent Group A>>

An alkyl group (preferably having 1 to 30 carbon atoms, more preferablyhaving 1 to 20 carbon atoms, and particularly preferably having 1 to 10carbon atoms; for example, methyl, ethyl, isopropyl, t-butyl, n-octyl,n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, and cyclohexyl), analkenyl group (preferably having 2 to 30 carbon atoms, more preferablyhaving 2 to 20 carbon atoms, and particularly preferably having 2 to 10carbon atoms; for example, vinyl, allyl, 2-butenyl, and 3-pentenyl), analkynyl group (preferably having 2 to 30 carbon atoms, more preferablyhaving 2 to 20 carbon atoms, and particularly preferably having 2 to 10carbon atoms; for example, propargyl and 3-pentynyl), an aryl group(preferably having 6 to 30 carbon atoms, more preferably having 6 to 20carbon atoms, and particularly preferably having 6 to 12 carbon atoms;for example, phenyl, p-methylphenyl, naphthyl, and anthranyl), an aminogroup (the amino group may have a substituent, and the total number ofcarbon atoms of the amino group including the substituent is preferablyfrom 0 to 30, more preferably from 0 to 20, and particularly preferablyfrom 0 to 10; the amino group is, for example, amino, methylamino,dimethylamino, diethylamino, dibenzylamino, diphenylamino, andditolylamino), an alkoxy group (preferably having 1 to 30 carbon atoms,more preferably having 1 to 20 carbon atoms, and particularly preferablyhaving 1 to 10 carbon atoms; for example, methoxy, ethoxy, butoxy, and2-ethylhexyloxy), and aryloxy group (preferably having 6 to 30 carbonatoms, more preferably having 6 to 20 carbon atoms, and particularlypreferably having 6 to 12 carbon atoms; for example, phenyloxy,1-naphthyloxy, and 2-naphthyloxy), a heterocyclic oxy group (preferablyhaving 1 to 30 carbon atoms, more preferably having 1 to 20 carbonatoms, and particularly preferably having 1 to carbon atoms; forexample, pyridyloxy, pyrazyloxy, pyrimidyloxy, and quinolyloxy), an acylgroup (preferably having 2 to 30 carbon atoms, more preferably having 2to 20 carbon atoms, and particularly preferably having 2 to 12 carbonatoms; for example, acetyl, benzoyl, formyl, and pivaloyl), analkoxycarbonyl group (preferably having 2 to 30 carbon atoms, morepreferably having 2 to 20 carbon atoms, and particularly preferablyhaving 2 to 12 carbon atoms; for example, methoxycarbonyl andethoxycarbonyl), an aryloxycarbonyl group (preferably having 7 to 30carbon atoms, more preferably having 7 to 20 carbon atoms, andparticularly preferably having 7 to 12 carbon atoms; for example,phenyloxycarbonyl), an acyloxy group (preferably having 2 to 30 carbonatoms, more preferably having 2 to 20 carbon atoms, and particularlypreferably having 2 to 10 carbon atoms; for example, acetoxy andbenzoyloxy), an acylamino group (preferably having 2 to 30 carbon atoms,more preferably having 2 to 20 carbon atoms, and particularly preferablyhaving 2 to 10 carbon atoms; for example, acetylamino and benzoylamino),an alkoxycarbonylamino group (preferably having 2 to 30 carbon atoms,more preferably having 2 to 20 carbon atoms, and particularly preferablyhaving 2 to carbon atoms; for example, methoxycarbonylamino), anaryloxycarbonylamino group (preferably having 7 to 30 carbon atoms, morepreferably having 7 to 20 carbon atoms, and particularly preferablyhaving 7 to 12 carbon atoms; for example, phenyloxycarbonylamino), asulfonylamino group (preferably having 1 to 30 carbon atoms, morepreferably having 1 to 20 carbon atoms, and particularly preferablyhaving 1 to carbon atoms; for example, methanesulfonylamino andbenzenesulfonylamino), a sulfamoyl group (preferably having 0 to 30carbon atoms, more preferably having 0 to 20 carbon atoms, andparticularly preferably having 0 to 12 carbon atoms; for example,sulfamoyl, methylsulfamoyl, dimethylsulfamoyl, and phenylsulfamoyl), acarbamoyl group (preferably having 1 to 30 carbon atoms, more preferablyhaving 1 to 20 carbon atoms, and particularly preferably having 1 to 12carbon atoms; for example, carbamoyl, methylcarbamoyl, diethylcarbamoyl,and phenylcarbamoyl), an alkylthio group (preferably having 1 to 30carbon atoms, more preferably having 1 to 20 carbon atoms, andparticularly preferably having 1 to 12 carbon atoms; for example,methylthio and ethylthio), an arylthio group (preferably having 6 to 30carbon atoms, more preferably having 6 to 20 carbon atoms, andparticularly preferably having 6 to 12 carbon atoms; for example,phenylthio), a heterocyclic thio group (preferably having 1 to 30 carbonatoms, more preferably having 1 to 20 carbon atoms, and particularlypreferably having to 12 carbon atoms; for example, pyridylthio,2-benzoimizolylthio, 2-benzoxazolylthio, and 2-benzothiazolylthio), asulfonyl group (preferably having 1 to 30 carbon atoms, more preferablyhaving 1 to 20 carbon atoms, and particularly preferably having 1 to 12carbon atoms; for example, mesyl and tosyl), a sulfinyl group(preferably having 1 to 30 carbon atoms, more preferably having 1 to 20carbon atoms, and particularly preferably having 1 to 12 carbon atoms;for example, methanesulfinyl and benzenesulfinyl), a ureido group(preferably having 1 to 30 carbon atoms, more preferably having 1 to 20carbon atoms, and particularly preferably having 1 to 12 carbon atoms;for example, ureido, methylureido, and phenylureido), a phosphoramidegroup (preferably having 1 to 30 carbon atoms, more preferably having 1to 20 carbon atoms, and particularly preferably having 1 to 12 carbonatoms; for example, diethyl phosphoramide and phenyl phosphoramide), ahydroxyl group, a mercapto group, a halogen atom (for example, afluorine atom, a chlorine atom, a bromine atom, and an iodine atom), acyano group, a sulfo group, a carboxyl group, a nitro group, ahydroxamic group, a sulfino group, a hydrazino group, an imino group, aheterocyclic group (inclusive of an aromatic heterocyclic group, whichpreferably has 1 to 30 carbon atoms, and more preferably 1 to 12 carbonatoms and in which examples of the hetero atom include a nitrogen atom,an oxygen atom, a sulfur atom, a phosphorus atom, a silicon atom, aselenium atom, and a tellurium atom; and specific examples thereofinclude pyridyl, pyrazinyl, pyrimidyl, pyridazinyl, pyrrolyl, pyrazolyl,triazolyl, imidazolyl, oxazolyl, triazolyl, isoxazolyl, isothiazolyl,quinolyl, furyl, thienyl, selenophenyl, tellurophenyl, piperidyl,piperidino, morpholino, pyrrolidyl, pyrrolidino, benzoxazolyl,benzoimidazolyl, benzothiazolyl, a carbazolyl group, an azepinyl group,and a silolyl group), a silyl group (the silyl group may have asubstituent, and the total number of carbon atoms of the silyl groupincluding the substituent is preferably from 3 to 40, more preferablyfrom 3 to 30, and particularly preferably from 3 to 24; the silyl groupis, for example, trimethylsilyl, triphenylsilyl, andphenyldimethylsilyl), a silyloxy group (preferably having 3 to 40 carbonatoms, more preferably having 3 to 30 carbon atoms, and particularlypreferably having 3 to 24 carbon atoms; for example, trimethylsilyloxyand triphenylsilyloxy), and a phosphoryl group (for example, adiphenylphosphoryl group and a dimethylphosphoryl group).

R¹ to R¹⁴ are each independently preferably a hydrogen atom, a deuteriumatom, an alkyl group, an aryl group, a heteroaryl group, a fluorineatom, a cyano group, an amino group, an alkoxy group, an aryloxy group,or a thio group, more preferably a hydrogen atom, an alkyl group, anaryl group, an amino group, or an alkoxy group, and particularlypreferably a hydrogen atom, an alkyl group, an aryl group, or an aminogroup.

For R¹ to R¹⁴, adjacent substituents may be bonded to each other to forma ring, and in the case of forming a ring, they preferably form analiphatic ring or a non-aromatic hetero ring, and more preferably form anon-aromatic nitrogen atom-containing hetero ring.

For the organic electroluminescent element of the present invention, itis preferable that at least one of R¹ to R¹⁴ in the general formula (1)be an electron donating substituent. Here, in the present specification,the electron donating substituent refers to a “substituent having σ_(p)denoting a negative value in the Hammett's law”.

Examples of the electron donating substituent include an amino group, analkoxy group, an aryloxy group, an alkylthio group, and an arylthiogroup, and above all, an amino group, an alkoxy group, and an aryloxygroup are preferable. For the organic electroluminescent element of thepresent invention, it is particularly preferable that at least one of R¹to R¹⁴ in the general formula (1) be an amino group.

The position of the electron donating substituent is preferably at leastone of R¹ to R³ and R⁸ to R¹⁹ in the general formula (1). Above all, inthe case where the position of the electron donating substituent is atleast one of R² and R⁹ in the general formula (1), when R² has theelectron donating substituent, R² is preferably fused with R¹ or R³ toform a ring, and when R⁹ has the electron donating substituent, R⁹ ispreferably fused with R⁸ or R¹⁰ to form a ring.

Further, the position of the electron donating substituent is morepreferably at least one of R¹, R³, R⁸ and R¹⁰ in the general formula(1).

By incorporating the electron donating substituent in such a position,the wavelength of the luminescent compound represented by the generalformula (1) can be shortened, thereby increasing the blue color purity.

For the organic electroluminescent element of the present invention, theluminescent compound represented by the general formula (1) ispreferably the luminescent compound represented by the general formula(2) or the luminescent compound represented by the general formula (3).

First, a case where the luminescent compound represented by the generalformula (1) is the luminescent compound represented by the generalformula (2) will be described.

(In the formula, R² to R¹⁴ each independently represent a hydrogen atom,a deuterium atom, an alkyl group, an aryl group, a heteroaryl group, afluorine atom, a cyano group, an amino group, an alkoxy group, anaryloxy group, a thio group, or a silyl group, and these may be bondedto each other to form a ring. R¹⁵ and R¹⁶ each independently representan alkyl group, an aryl group, a heteroaryl group, or a hydrogen atom,and may be bonded to each other to form a ring or may be bonded to R² orR¹⁴ to form a ring.)

In the general formula (2), R² to R¹⁴ each independently represent ahydrogen atom, a deuterium atom, an alkyl group, an aryl group, aheteroaryl group, a fluorine atom, a cyano group, an amino group, analkoxy group, an aryloxy group, a thio group, or a silyl group, andthese may be bonded to each other to form a ring. The preferred rangesof R² to R¹⁴ in the general formula (2) are the same as the preferredranges of R² to R¹⁴ in the general formula (1).

In the general formula (2), R¹⁵ and R¹⁶ each independently represent analkyl group, an aryl group, a heteroaryl group, or a hydrogen atom, andmay be bonded to each other to form a ring or may be bonded to R² or R¹⁴to form a ring.

The preferred ranges of R¹⁵ and R¹⁶ are the same as in the descriptionof the amino group in the Substituent a as described above.

In the case where R¹⁵ and R¹⁶ form a ring, they are preferably bonded toeach other to form a ring or bonded to R² to form a ring, and they aremore preferably bonded to R² to form a ring. Further, in the case whereR¹⁵ and R¹⁶ are bonded to each other to form a ring, they preferablyform a pyrrole skeleton or a carbazole skeleton.

R¹⁵ and R¹⁶ are more preferably a substituted or unsubstituted arylgroup, and R¹⁵ and R¹⁶ are particularly preferably a substituted orunsubstituted phenyl group. More particularly preferred cases include acase where R¹⁵ and R¹⁶ are both phenyl groups having a substituent fromthe viewpoint of inhibition of association, or a case where any one ofR¹⁵ and R¹⁶ are a phenyl group having a substituent and are combinedwith R² to be subjected to ring fusion, and further, the other is aphenyl group having a substituent.

The substituent which R¹⁵ and R¹⁶ further have is preferably an alkylgroup or an aryl group, more preferably an alkyl group having 1 to 3carbon atoms, or a phenyl group, particularly preferably a methyl groupor an isopropyl group, and more particularly preferably a methyl group.Further, the R¹⁵ and R¹⁶ may have a plurality of substituents, and forexample, in the case where R¹⁵ and R¹⁶ are phenyl groups, they arepreferably ones having 1 or 2 substituents.

The luminescent compound represented by the general formula (2) ispreferably one further having the electron donating substituent in atleast one of R³ and R⁸ to R¹⁰, and in more preferred aspect, theluminescent compound represented by the general formula (2) has an arylgroup in R⁹, or an amino group in at least one of R³, R⁸, and R¹⁰.

In the case of an aspect in which the luminescent compound representedby the general formula (2) has an aryl in R⁹, R⁹ is preferably an arylgroup having a substituent, and the substituent is more preferably analkyl group, and particularly preferably a methyl group. Further, inthis case, R⁹ is preferably an aryl group having a plurality of thesubstituents, more preferably an aryl group having 1 to 3 substituents,and particularly preferably an aryl group having 2 substituents.

On the other hand, in the case of an aspect in which the luminescentcompound represented by the general formula (2) has an amino group in atleast one of R³, R⁸ and R¹⁰, for the organic electroluminescent elementof the present invention, the luminescent compound represented by thegeneral formula (1) is preferably a luminescent compound represented bythe following general formula (5), (6), or (7).

(In the formula, R² to R⁷ and R⁹ to R¹⁴ each independently represent ahydrogen atom, a deuterium atom, an alkyl group, an aryl group, aheteroaryl group, a fluorine atom, a cyano group, an amino group, analkoxy group, an aryloxy group, a thio group, or a silyl group, andthese may be bonded to each other to form a ring. R¹⁷ to R²⁰ eachindependently represent alkyl group, an aryl group, a heteroaryl group,or a hydrogen atom, and R¹⁷ and R¹⁹ may be bonded to any of R², R¹⁴, orR¹⁸ and any of R⁷, R⁹, or R²⁰, respectively, to form a ring.)

R² to R⁷ and R⁹ to R²⁴ in the general formula (5) have the samedefinitions as R² to R⁷ and R⁹ to R¹⁴ in the general formula (1). Aboveall, R² to R⁷ and R⁹ to R¹⁴ in the general formula (5) are eachindependently preferably a hydrogen atom, a deuterium atom, an alkylgroup, an aryl group, a fluorine atom, a cyano group, or an alkoxygroup, more preferably a hydrogen atom, an alkyl group, or an arylgroup, and particularly preferably a hydrogen atom.

R¹⁷ to R²⁰ in the general formula (5) each independently represent analkyl group, an aryl group, a heteroaryl group, or a hydrogen atom. Inthe case where R¹⁷ and R¹⁸ form a ring, they are preferably bonded toeach other to form a ring or bonded to R² to form a ring, and they aremore preferably bonded to R² to form a ring. Further, in the case whereR¹⁷ and R¹⁸ are bonded to each other to form a ring, they preferablyform a pyrrole skeleton or a carbazole skeleton. R¹⁷ and R¹⁸ are morepreferably a substituted or unsubstituted aryl group, and particularlypreferably a substituted or unsubstituted phenyl group. The ranges ofthe substituents which R¹⁷ and R¹⁸ further have are the same as theranges of the substituents which R¹⁵ and R¹⁶ in the general formula (2)further have.

In the case where R¹⁹ and R²⁰ form a ring, they are preferably bonded toeach other to form a ring or bonded to R⁹ to form a ring, and they aremore preferably bonded to R⁹ to form a ring. Further, in the case whereR¹⁹ and R²⁰ are bonded to each other to form a ring, they preferablyform a pyrrole skeleton or a carbazole skeleton. R¹⁹ and R²⁰ are morepreferably a substituted or unsubstituted aryl group, and particularlypreferably a substituted or unsubstituted phenyl group. The ranges ofthe substituents which R¹⁹ and R²⁰ further have are the same as theranges of the substituents which R¹⁵ and R¹⁶ in the general formula (2)further have.

(In the formula, R² to R⁹ and R¹¹ to R¹⁴ each independently represent ahydrogen atom, a deuterium atom, an alkyl group, an aryl group, aheteroaryl group, a fluorine atom, a cyano group, an amino group, analkoxy group, an aryloxy group, a thio group, or a silyl group, andthese may be bonded to each other to form a ring. R²¹ to R²⁴ eachindependently represent alkyl group, an aryl group, a heteroaryl group,or a hydrogen atom, and R²¹ and R²³ may be bonded to any of R², or R¹⁴,or R²² and any of R⁹, R¹¹, or R²⁴, respectively, to form a ring.)

R² to R⁹ and R¹¹ to R¹⁴ in the general formula (6) have the samedefinitions as R² to R⁹ and R¹¹ to R¹⁴ in the general formula (1). Aboveall, R² to R⁹ and R¹¹ to R¹⁴ in the general formula (6) are eachindependently preferably a hydrogen atom, a deuterium atom, an alkylgroup, an aryl group, a fluorine atom, a cyano group, or an alkoxygroup, and more preferably a hydrogen atom or an alkyl group.

R²¹ to R²⁴ in the general formula (6) each independently represent analkyl group, an aryl group, a heteroaryl group, or a hydrogen atom.Preferably, R²¹ and R²² do not form a ring. R²¹ and R²² are morepreferably a substituted or unsubstituted aryl group, and particularlypreferably a substituted or unsubstituted phenyl group. The ranges ofthe substituents which R²¹ and R²² further have are the same as theranges of the substituents which R¹⁵ and R¹⁶ in the general formula (2)further have

In the case where R²³ and R²⁴ form a ring, they are preferably bonded toeach other to form a ring or bonded to R⁹ to form a ring, and they aremore preferably bonded to R⁹ to form a ring. Further, in the case whereR²³ and R²⁴ are bonded to each other to form a ring, they preferablyform a pyrrole skeleton or a carbazole skeleton. R²³ and R²⁴ are morepreferably a substituted or unsubstituted aryl group, and particularlypreferably a substituted or unsubstituted phenyl group. The ranges ofthe substituents which R²³ and R²⁴ further have are the same as theranges of the substituents which R¹⁵ and R¹⁶ in the general formula (2)further have.

(In the formula, R² and R⁴ to R¹⁴ each independently represent ahydrogen atom, a deuterium atom, an alkyl group, an aryl group, aheteroaryl group, a fluorine atom, a cyano group, an amino group, analkoxy group, an aryloxy group, a thio group, or a silyl group, andthese may be bonded to each other to form a ring. R²⁵ to R²⁸ eachindependently represent an alkyl group, an aryl group, a heteroarylgroup, or a hydrogen atom, and R²⁵ and R²⁷ may be bonded to any of R²,R¹⁴ or R²⁶ and any of R², R⁴ or R²⁸, respectively, to form a ring.)

R² and R⁴ to R¹⁴ in the general formula (7) have the same definitions asR² and R⁴ to R¹⁴ in the general formula (1). Above all, R² and R⁴ to R¹⁴in the general formula (7) are each independently preferably a hydrogenatom, a deuterium atom, an alkyl group, an aryl group, a fluorine atom,a cyano group, or an alkoxy group, and more preferably a hydrogen atomor an aryl group.

R²⁵ to R²⁸ in the general formula (7) each independently represent analkyl group, an aryl group, a heteroaryl group, or a hydrogen atom.Preferably, R²⁵ and R²⁶ do not form a ring. R²⁵ and R²⁶ are morepreferably a substituted or unsubstituted aryl group, and particularlypreferably a substituted or unsubstituted phenyl group. In a moreparticularly preferable case, R²⁵ and R²⁶ are both substituted phenylgroups. The ranges of the substituents which R²⁵ and R²⁶ further haveare the same as the ranges of the substituents which R¹⁵ and R¹⁶ in thegeneral formula (2) further have.

Preferably, R²⁷ and R²⁸ do not form a ring. R²⁷ and R²⁸ are morepreferably a substituted or unsubstituted aryl group, and particularlypreferably a substituted or unsubstituted phenyl group. A moreparticularly preferred case is a case where R²³ and R²⁴ are bothsubstituted phenyl groups. The ranges of the substituents which R²⁷ andR²⁸ further have are the same as the ranges of the substituents whichR¹⁵ and R¹⁶ in the general formula (2) further have.

Among the luminescent compounds represented by the general formulae (5)to (7), the luminescent compound represented by the general formula (5)or (7) is more preferred, and the compound represented by the generalformula (5) is particularly preferred.

Next, a case where the luminescent compound represented by the generalformula (1) is the luminescent compound represented by the generalformula (3) will be described.

(In the formula, R¹ and R⁴ to R¹⁴ each independently represent ahydrogen atom, a deuterium atom, an alkyl group, an aryl group, aheteroaryl group, a fluorine atom, a cyano group, an amino group, analkoxy group, an aryloxy group, a thio group, or a silyl group, andthese may be bonded to each other to form a ring. R³¹ to R³³ eachindependently represent an alkyl group, an aryl group, a heteroarylgroup, or a hydrogen atom, and R³² and R³³ may be bonded to each otherto form a ring.)

R¹ and R⁴ to R¹⁴ in the general formula (3) have the same definitions asR¹ and R⁴ to R¹⁴ in the general formula (1). Above all, R¹ and R⁴ to R¹⁴in the general formula (3) are each independently preferably a hydrogenatom, a deuterium atom, an alkyl group, an aryl group, a fluorine atom,a cyano group, an amino group, or an alkoxy group, more preferably ahydrogen atom, an alkyl group, an aryl group, or an amino group, andparticularly preferably a hydrogen atom or one having an amino group.

In the general formula (3), R³¹ to R³³ each independently represent analkyl group, an aryl group, a heteroaryl group, or a hydrogen atom, andR³² and R³³ may be bonded to each other to form a ring.

It is preferable that each substituent other than the hydrogen atom andthe deuterium atom represented by R³¹ be specifically the followingSubstituent Group b.

<<Substituent Group b>>

An alkyl group (preferably having 1 to 30 carbon atoms, more preferablyhaving 1 to 20 carbon atoms, and particularly preferably having 1 to 10carbon atoms; for example, methyl, ethyl, isopropyl, t-butyl, n-octyl,n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, and cyclohexyl), an arylgroup (preferably having 6 to 30 carbon atoms, more preferably having 6to 20 carbon atoms, and particularly preferably having 6 to 12 carbonatoms; for example, phenyl, p-methylphenyl, naphthyl, and anthranyl),and a heteroaryl group (preferably having 1 to 30 carbon atoms, and morepreferably having 1 to 12 carbon atoms, in which examples of the heteroatom include a nitrogen atom, an oxygen atom, a sulfur atom, aphosphorus atom, a silicon atom, a selenium atom, and a tellurium atom;and specific examples thereof include pyridyl, pyrazinyl, pyrimidyl,pyridazinyl, pyrrolyl, pyrazolyl, triazolyl, imidazolyl, oxazolyl,triazolyl, isoxazolyl, isothiazolyl, quinolyl, furyl, thienyl,selenophenyl, tellurophenyl, piperidyl, piperidino, morpholino,pyrrolidyl, pyrrolidino, benzoxazolyl, benzoimidazolyl, benzothiazolyl,a carbazolyl group, an azepinyl group, and a silolyl group). Thesesubstituents may be further substituted, and examples of the additionalsubstituent include the groups selected from the Substituent Group B.Further, the substituent substituted with a substituent may be furthersubstituted, and examples of the additional substituent include thegroups selected from the Substituent Group B as described above. Inaddition, the substituent substituted with the substituent which hasbeen substituted with a substituent may be further substituted, andexamples of the additional substituent include the groups selected fromthe Substituent Group b as described above.

R³¹ is preferably an alkyl group, a perfluoroalkyl group, an aryl group,a heteroaryl group, or a fluorine atom, and more preferably any one of alinear, branched, or cyclic alkyl group having 1 to 10 carbon atoms; anaryl group having 6 to 50 carbon atoms; and a heteroaryl group having 5to 20 carbon atoms and containing at least any one of N, O, and S as ahetero atom. R³¹ is particularly preferably an aryl group having 6 to 14carbon atoms, and more particularly preferably a substituted phenylgroup. Examples of the substituent which an aryl group having 6 to 14carbon atoms may have include a linear or branched alkyl group having 1to 10 carbon atoms, and preferably, for example methyl, ethyl,isopropyl, t-butyl, n-octyl, and n-decyl.

Examples of R³² and R³³ (the substituents on carbon atoms) include theSubstituent Group A.

R³² and R³³ each independently preferably represent an alkyl group, anaryl group, a heteroaryl group, a perfluoroalkyl group, an alkoxy group,or a fluorine atom, and more preferably an alkyl group, an aryl group,and a heteroaryl group. R³² and R³³ each independently particularlypreferably represent any one of an a linear, branched, or cyclic alkylgroup having 1 to 10 carbon atoms; an aryl group having 6 to 14 carbonatoms; and a heteroaryl group having 5 to 20 carbon atoms and containingat least any one of N, O, and S as a hetero atom); and more particularlypreferably a linear or branched alkyl group having 1 to 6 carbon atoms.In addition, from the viewpoint of easiness of synthesis, it ispreferable that R³² and R³³ be the same substituents as each other.

R³² and R³³ may be combined with each other to form a 5- or 6-memberedring, and the 5- or 6-membered ring thus formed may be anyone of abenzene ring, a heteroaryl ring, a cycloalkyl ring, a cycloalkenyl ring,and a hetero ring. The 5- or 6-membered ring thus formed may be any oneof a cycloalkenyl ring, a benzene ring, and a heteroaryl ring. Examplesof the heteroaryl ring include those containing 1 to 3 hetero atomsselected from the group consisting of a nitrogen atom, an oxygen atom,and a sulfur atom in the ring-constituting atoms. Specific examplesthereof include a pyridine ring, a pyrazine ring, a pyridazine ring, apyrimidine ring, an imidazole ring, an oxazole ring, a thiazole ring, apyrazole ring, a thiophene ring, and a furan ring. The 5- or 6-memberedring thus formed may have a substituent, examples of the substituent onthe carbon atom include the Substituent Group A, and examples of thesubstituent on the nitrogen atom include the Substituent Group B. The 5-or 6-membered ring thus formed is preferably a benzene ring, and morepreferably an unsubstituted benzene ring.

The luminescent compound represented by the general formula (1) ispreferably a luminescent compound represented by the following generalformula (4) among the luminescent compounds represented by the generalformula (3).

(In the formula, R¹, R⁴ to R⁸ and R¹¹ to R¹⁴ each independentlyrepresent a hydrogen atom, a deuterium atom, an alkyl group, an arylgroup, a heteroaryl group, a fluorine atom, a cyano group, an aminogroup, an alkoxy group, an aryloxy group, a thio group, or a silylgroup, and these may be bonded to each other to form a ring. R³¹ to R³⁶each independently represent an alkyl group, an aryl group, a heteroarylgroup, or a hydrogen atom, R³² and R³³ may be bonded to each other toform a ring, and R³⁵ and R³⁶ may be bonded to each other to form aring.)

R¹, R⁴ to R⁸ and R¹¹ to R¹⁴ in the general formula (4) have the samedefinitions as R¹, R⁴ to R⁸ and R¹¹ to R¹⁴ in the general formula (1).Above all, R¹, R⁴ to R⁸ and R¹¹ to R¹⁴ in the general formula (4) areeach independently preferably a hydrogen atom, a deuterium atom, analkyl group, an aryl group, a fluorine atom, a cyano group, or an alkoxygroup, more preferably a hydrogen atom, an alkyl group, or an arylgroup, and particularly preferably a hydrogen atom.

In the general formula (4), R³¹ to R³³ have the same definitions as R³¹to R³³ in the general formula (3), and the preferred ranges thereof arealso the same. R³⁴ to R³⁶ each independently represent an alkyl group,an aryl group, a heteroaryl group, or a hydrogen atom, and R³⁵ and R³⁶may be bonded to each other to form a ring.

The preferred range of R³⁴ is the same as the preferred range of R³¹ inthe general formula (3). The preferred ranges of R³⁵ and R³⁶ are thesame as the preferred ranges of R³² and R³³ in the general formula (3).

The maximum light emitting wavelength of the organic electroluminescentelement using the luminescent compound represented by the generalformula (1) is usually less than 455 nm, preferably 400 nm or more andless than 455 nm, more preferably 420 nm or more and less than 455 nm,still more preferably 430 nm or more and less than 455 nm, and mostpreferably 440 nm or more and less than 455 nm, from the viewpoint ofobtaining blue light emission with high color purity.

The molecular weight of the luminescent compound represented by thegeneral formula (1) is preferably 1000 or less, more preferably 900 orless, particularly preferably 850 or less, and still more preferably 800or less. By reducing the molecular weight, the sublimation temperaturecan be lowered, and thus, it is possible to prevent the thermaldecomposition of the compound by deposition. Further, the energyrequired for deposition can be suppressed by decreasing the depositiontime. Here, since a material having a high sublimation temperature canundergo thermal decomposition during long-term deposition, it isfavorable that the sublimation temperature be not too high from theviewpoint of deposition suitability. The sublimation temperature (whichmeans a temperature which leads to reduction by 10% by mass in thepresent specification) of the luminescent compound represented by thegeneral formula (1) is preferably 300° C., more preferably 285° C. orlower, and still more preferably 270° C. or lower.

Specific examples of the luminescent compound represented by the generalformula (1) are shown below, but it should not be construed that theluminescent compound represented by the general formula (1) which can beused in the present invention is limited to these specific examples.

The luminescent compound represented by the general formula (1) can besynthesized by the method described in Org. Lett., 2003, 2587, or thelike, or a combination of other known methods. In addition, for example,it can also be synthesized by a combination of the following schemes.

Synthesis intermediates having various substituents can be synthesizedby a combination of known reactions. Further, for the reaction in eachstep, the synthesis can be carried out using the conditions describedin, for example, Org. Synth., III, 339, (1955) for Ullmann coupling. Thesubsequent step for a reduction reaction can be carried out under thereaction conditions described in, for example, J. Org. Chem., 1993, 58,1666.

For a Sandmeyer reaction, the synthesis can be carried out by the methoddescribed in, for example, J. Org. Chem., 1987, 52, 1339. For a Suzukicoupling, the synthesis can be carried out by the method described in,for example, Bioorg. Med. Chem. Lett., 2007, 17, 5233. For a ringclosing reaction by a Pd catalyst, the synthesis can be carried out bythe method described in, for example, J. Am. Chem. Soc., 2006, 128, 581.The subsequent deprotection and TfO-addition can be carried out underthe reaction conditions described in, for example, Tetrahedron, 2001,57, 9575. The subsequent coupling reaction by a Pd catatlyst can becarried out under the reaction conditions described in, for example, J.Org. Chem., 2011, 1054. Further, each of the substituents may beintroduced in any stage for the intermediate.

After the synthesis, purification is preferably carried out by columnchromatography, recrystallization, or the like, and then by sublimationpurification. By the sublimation purification, organic impurities can beseparated and inorganic salts, residual solvents, or the like can beremoved effectively.

The maximum light emitting wavelength of the light emitting material foran organic electroluminescent element, represented by general formula(1) is preferably less than 455 nm, more preferably from 400 nm to 455nm, particularly preferably 420 nm or more and less than 455 nm, stillmore preferably 430 nm or more and less than 455 nm, and most preferably440 nm or more and less than 455 nm.

[Configuration of Organic Electroluminescent Element]

The organic electroluminescent element of the present invention has asubstrate, a pair of electrodes including an anode and a cathode,disposed on the substrate, and at least one organic layer including alight emitting layer, disposed between the electrodes, in which thelight emitting layer contains the luminescent compound represented bythe general formula (1).

The configuration of the organic electroluminescent element of thepresent invention is not particularly limited. FIG. 1 shows an exampleof the configuration of the organic electroluminescent element of thepresent invention. An organic electroluminescent element 10 in FIG. 1includes organic layers between a pair of electrodes (an anode 3 and acathode 9) on a substrate 2.

The element configuration, the substrate, the anode, and the cathode ofthe organic electroluminescent element are described in detail, forexample, in JP-A-2008-270736, and the matters described in the patentpublication can be applied to the present invention.

Hereinafter, preferred embodiments of the organic electroluminescentelement of the present invention will be described in detail, in theorder of the substrate, the electrode, the organic layer, the protectivelayer, the sealing enclosure, the driving method, the light emittingwavelength, and applications thereof.

<Substrate>

The organic electroluminescent element of the present invention has asubstrate.

The substrate used in the present invention is preferably a substratethat does not scatter or attenuate light emitted from the organic layer.In the case of an organic material, those having excellent heatresistance, dimensional stability, solvent resistance, electricalinsulating properties, and processability are preferred.

<Electrodes>

The organic electroluminescent element of the present invention has apair of electrodes including an anode and a cathode, disposed on thesubstrate.

In view of the properties of the light emitting element, at least oneelectrode of a pair of electrodes, the anode and the cathode, ispreferably transparent or semi-transparent.

(Anode)

The anode may be typically one having a function as an electrode ofsupplying holes into an organic layer, and is not particularly limitedin its shape, structure, size, or the like. Further, depending on theuse and purpose of the light emitting element, the anode can be suitablyselected from the known electrode materials. As described above, theanode is usually provided as a transparent anode.

(Cathode)

The cathode may be typically one having a function as an electrode ofinjecting electrons to an organic layer, and is not particularly limitedin its shape, structure, size, or the like. Further, depending on theuse and purpose of the light emitting element, the cathode can besuitably selected from the known electrode materials.

<Organic Layer>

The organic electroluminescent element of the present invention includesat least one layer of the organic layer(s) including the light emittinglayers disposed between the electrodes, in which the light emittinglayer contains the luminescent compound represented by the generalformula (1).

The organic layer is not particularly limited and can be suitablyselected depending on the use and purpose of the organicelectroluminescent element. However, the organic layer is preferablyformed on the transparent electrode or the semi-transparent electrode.In that case, the organic layer is formed on the whole surface or onesurface of the transparent electrode or the semi-transparent electrode.

The shape, the size, the thickness, and the like of the organic layerare not particularly limited and can be suitably selected depending onthe purpose.

Hereinafter, the configuration of the organic layer, the method forforming an organic layer, preferred aspects of the respective layersconstituting the organic layer, and the materials used in the respectivelayers in the organic electroluminescent element of the presentinvention will be described in order.

(Configuration of Organic Layers)

In the organic electroluminescent element of the present invention, theorganic layer includes a light emitting layer.

Furthermore, the organic layer preferably includes a charge transportinglayer. The charge transporting layer refers to a layer in which chargesmove when voltage is applied to the organic electroluminescent element.Specifically, examples thereof include a hole injecting layer, a holetransporting layer, an electron blocking layer, a light emitting layer,a hole blocking layer, an electron transporting layer, and an electroninjecting layer. When the charge transporting layer is a hole injectinglayer, a hole transporting layer, an electron blocking layer, or a lightemitting layer, an organic electroluminescent element can be preparedwith low cost and high efficiency.

The luminescent compound represented by the general formula (1) iscontained in the light emitting layers in the organic layers disposedbetween the electrodes of the organic electroluminescent element.

However, the luminescent compound represented by the general formula (1)may be contained in another organic layer of the organicelectroluminescent element of the present invention. Examples of theorganic layer other than the light emitting layer, which may contain theluminescent compound represented by the general formula (1), include ahole injecting layer, a hole transporting layer, an electrontransporting layer, an electron injecting layer, an exciton blockinglayer, and a charge blocking layer (a hole blocking layer, an electronblocking layer, or the like), preferably any one of an exciton blockinglayer, a charge blocking layer, an electron transporting layer, and anelectron injecting layer, and more preferably an exciton blocking layer,a charge blocking layer, or an electron transporting layer.

The luminescent compound represented by the general formula (1) iscontained in the amount of preferably 0.1% by mass to 100% by mass, morepreferably 1% by mass to 50% by mass, and still more preferably 2% bymass to 20% by mass, with respect to the total mass of the lightemitting layer.

In the case where the luminescent compound represented by the generalformula (1) is contained in an organic layer other than the lightemitting layer, the luminescent compound represented by the generalformula (1) is contained in the amount of preferably 70% by mass to 100%by mass, more preferably 80% by mass to 100% by mass, and still morepreferably 90% by mass to 100% by mass, with respect to the total massof the organic layer.

(Method for Forming Organic Layers)

Each of the organic layers in the organic electroluminescent element ofthe present invention can be suitably formed by any of dry type filmforming methods such as a deposition method and a sputtering method, andwet type film forming methods (solution coating methods) such as atransfer method, a printing method, a spin coating method, and a barcoating method.

In the organic electroluminescent element of the present invention, thelight emitting layer disposed between the pair of electrodes ispreferably formed by a vacuum deposition process or a wet process.Further, the light emitting layer is more preferably formed bydeposition of a composition containing the luminescent compoundrepresented by the general formula (1) in at least one layer.

(Light Emitting Layer)

The light emitting layer is a layer having a function of, uponapplication of an electric field, receiving holes from the anode, thehole injecting layer, or the hole transporting layer, receivingelectrons from the cathode, the electron injecting layer, or theelectron transporting layer, providing a recombination site of the holesand the electrons, and causing light emitting. However, the lightemitting layer in the present invention is not necessarily limited tothe light emitting by such a mechanism.

The light emitting layer in the organic electroluminescent element ofthe present invention may be constituted of only the light emittingmaterial, or may be constituted as a mixed layer of a host material andthe light emitting material. The light emitting material may be made ofone kind or two or more kinds thereof. The host material is preferably acharge transporting material. The host material may be made of one kindor two or more kinds thereof. Examples thereof include a configurationin which an electron transporting host material and a hole transportinghost material are mixed. Further, the light emitting layer may include amaterial which does not have charge transporting properties and does notemit light.

In addition, the light emitting layer may be made of a single layer ormultiple layers of two or more layers. Each of the layers may includethe same light emitting material or host material, and may also includea different material in every layer. In the case where a plurality oflight emitting layers are present, each of the light emitting layers mayemit light in a different luminous color from each other.

The thickness of the light emitting layer is not particularly limited,but it is usually from 2 nm to 500 nm, and above all, from the viewpointof external quantum efficiency, it is more preferably from 3 nm to 200nm, and still more preferably from 5 nm to 100 nm.

In the organic electroluminescent element of the present invention, thelight emitting layer contains the luminescent compound represented bythe general formula (1), and the luminescent compound represented by thegeneral formula (1) is used as the light emitting material of the lightemitting layer. The host material used in the light emitting layer isnot particularly limited. Here, in the present specification, the hostmaterial is a compound which usually plays a role in injecting ortransporting charges in the light emitting layer and is also a compoundwhich does not substantially emit light in itself. As used herein, thestatement “which does not substantially emit light” means that theamount of light emission from the compound which does not substantiallyemit light is preferably 5% or less, more preferably 3% or less, andstill more preferably 1% or less, with respect to the total amount oflight emission in the whole of the element.

(Light Emitting Material)

In the organic electroluminescent element of the present invention, theluminescent compound represented by the general formula (1) ispreferably used as the light emitting material, but in this case, it ispossible to use the luminescent compound represented by the generalformula (1) in combination with light emitting materials different fromthe compound. Further, in the organic electroluminescent element of thepresent invention, in the case where the luminescent compoundrepresented by the general formula (1) is used as a host material of thelight emitting layer or in the case where the luminescent compoundrepresented by the general formula (1) is used in an organic layer otherthan the light emitting layer, a light emitting material different fromthe luminescent compound represented by the general formula (1) is usedin the light emitting layer.

The light emitting material which can be used in the present inventionmay be any one of a phosphorescent light emitting material, afluorescent light emitting material, and the like. Further, the lightemitting layer in the present invention may contain two or more kinds oflight emitting materials in order to improve the color purity or widenthe light emitting wavelength region.

The fluorescent light emitting material and the phosphorescent lightemitting material which can be used in the organic electroluminescentelement of the present invention are described in detail in, forexample, paragraph Nos. [0100] to [0164] of JP-A-2008-270736 andparagraph Nos. [0088] to [0090] of JP-A-2007-266458, and the detaileddescriptions in these publications can be applied to the presentinvention.

Examples of the phosphorescent light emitting material which can be usedin the present invention include phosphorescent light emitting compoundsdescribed in patent documents, for example, U.S. Pat. Nos. 6,303,238 and6,097,147, WO00/57676, WO00/70655, WO01/08230, WO01/39234, WO01/41512,WO02/02714, WO02/15645, WO02/44189, WO05/19373, JP-A-2001-247859,JP-A-2002-302671, JP-A-2002-117978, JP-A-2003-133074, JP-A-2002-235076,JP-A-2003-123982, JP-A-2002-170684, EP1211257, JP-A-2002-226495,JP-A-2002-234894, JP-A-2001-247859, JP-A-2001-298470, JP-A-2002-173674,JP-A-2002-203678, JP-A-2002-203679, JP-A-2004-357791, JP-A-2006-256999,JP-A-2007-19462, JP-A-2007-84635, and JP-A-2007-96259. Above all,examples of the light emitting material which is more preferred includephosphorescent light emitting metal complex compounds such as Ircomplexes, Pt complexes, Cu complexes, Re complexes, W complexes, Rhcomplexes, Ru complexes, Pd complexes, Os complexes, Eu complexes, Tbcomplexes, Gd complexes, Dy complexes, and Ce complexes, and Ircomplexes, Pt complexes, and Re complexes are particularly preferred.Above all, Ir complexes, Pt complexes, and Re complexes each includingat least one coordination mode of a metal-carbon bond, a metal-nitrogenbond, a metal-oxygen bond, and a metal-sulfur bond are preferred.Furthermore, from the viewpoints of luminous efficiency, drivingdurability, chromaticity, or the like, Ir complexes and Pt complexes areparticularly preferred, and Ir complexes are the most preferred.

The kind of the fluorescent light emitting material which can be used inthe present invention is not particularly limited, but examples thereofinclude those other than the luminescent compound represented by thegeneral formula (1), for example, benzoxazole, benzimidazole,benzothiazole, styrylbenzene, polyphenyl, diphenylbutadiene,tetraphenylbutadiene, naphthalimide, coumarin, pyrane, perinone,oxadiazole, aldazine, pyralizine, cyclopentadiene, bisstyrylanthracene,quinacridone, pyrrolopyridine, thiadiazolopyridine, cyclopentadiene,styrylamine, aromatic fused polycyclic compounds (anthracene,phenanthroline, pyrene, perylene, rubrene, pentacene, and the like), avariety of metal complexes typified by metal complexes of 8-quinolinol,pyrromethene complexes, and rare-earth complexes, polymer compounds suchas polythiophene, polyphenylene, and polyphenylenevinylene, organicsilanes, and derivatives thereof.

In addition, the compound described in paragraph No. of JP-A-2010-111620can also be used as a light emitting material.

The light emitting layer in the organic electroluminescent element ofthe present invention may be constituted with only a light emittingmaterial or may be constituted as a mixed layer of a host material and alight emitting material. The light emitting material may be made of onekind or two or more kinds. The host material is preferably a chargetransporting material. The host material may be made of one kind or twoor more kinds. Examples thereof include a configuration in which anelectron transporting host material and a hole transporting hostmaterial are mixed. Further, the light emitting layer may contain amaterial which does not have charge transporting properties and whichdoes not emit light.

In addition, the light emitting layer may be made of a single layer ortwo or more layers. Each of the layers may include the same lightemitting materials or host materials, and may also include differentmaterials from each other over layers. In the case where a plurality oflight emitting layers are present, each of the light emitting layers mayemit light in different luminous colors from each other.

(Host Material)

The host material is a compound that usually plays a role in injectingor transporting charges in the light emitting layer and is also acompound which does not substantially emit light in itself. As usedherein, the statement “which does not substantially emit light” meansthat the amount of light emission from the compound which does notsubstantially emit light is preferably 5% or less, more preferably 3% orless, and still more preferably 1% or less of the total amount of lightemitting in the whole of the element.

Examples of the host material which can be used in the organicelectroluminescent element of the present invention include thefollowing compounds, other than the luminescent compound represented bythe general formula (1):

conductive high-molecular oligomers such as pyrrole, indole, carbazole,azaindole, azacarbazole, triazole, oxazole, oxadiazole, pyrazole,imidazole, thiophene, benzothiophene, dibenzothiophene, furan,benzofuran, dibenzofuran, polyarylalkane, pyrazoline, pyrazolone,phenylenediamine, arylamine, amino-substituted chalcone,styrylanthracene, fluorenone, hydrazone, stilbene, silazane, aromatictertiary amine compounds, styrylamine compounds, porphyrin-basedcompounds, fused ring aromatic hydrocarbon compounds (fluorene,naphthalene, phenanthrene, triphenylene, and the like), polysilane-basedcompounds, poly(N-vinylcarbazole), aniline-based copolymers, thiopheneoligomers, and polythiophene, organic silanes, carbon films, pyridine,pyrimidine, triazine, imidazole, pyrazole, triazole, oxazole,oxadiazole, fluorenone, anthraquinodimethane, anthrone, diphenylquinone,thiopyran dioxide, carbodiimide, fluorenylidenemethane,distyrylpyrazine, fluorine-substituted aromatic compounds, heterocyclictetracarboxylic anhydrides such as naphthalene perylene, phthalocyanine,and a variety of metal complexes typified by metal complexes of8-quinolinol derivatives and metal complexes having metalphthalocyanine, benzoxazole, or benzothiazole as a ligand thereof, andderivatives thereof (which may have a substituent or a fused ring). Inaddition, the compounds described in paragraph No. [0081] or [0083] ofJP-A-2010-111620 can also be used.

Above all, carbazole, dibenzothiophene, dibenzofuran, arylamine,aromatic hydrocarbon compounds with fused rings, and metal complexes arepreferred, and aromatic hydrocarbon compounds with fused rings areparticularly preferred since they are stable. As the aromatichydrocarbon compounds with fused rings, naphthalene-based compounds,anthracene-based compounds, phenanthrene-based compounds,triphenylene-based compounds, and pyrene-based compounds are preferred;anthracene-based compounds and pyrene-based compounds are morepreferred; and anthracene-based compounds are particularly preferred. Asthe anthracene-based compounds, those described in paragraph Nos. [0033]to [0064] of WO 2010/134350 are particularly preferred, and examplesthereof include Compounds H-1 and H-2 as described later.

The host material that can be used in the light emitting layer in theorganic electroluminescent element of the present invention may be ahost material having hole transporting properties or a host materialhaving electron transporting properties.

In the light emitting layer, the singlet lowest excited energy (S₁energy) in the film state of the host material is preferably higher thanthe S₁ energy of the light emitting material from the viewpoints ofcolor purity, luminous efficiency, and driving durability. The S₁ of thehost material is higher than the S₁ of the light emitting materialpreferably by 0.1 eV or more, more preferably by 0.2 eV or more, andstill more preferably by 0.3 eV or more.

When S₁ in the film state of the host material is lower than S₁ of thelight emitting material, the light emitting is lost, and thus, the hostmaterial is required to have higher S₁ than the S₁ of the light emittingmaterial. Further, even in the case where S₁ of the host material ishigher than the S₁ of the light emitting material, a small difference inthe S₁ of the both leads to partial reverse energy movement from thelight emitting material to the host material, which causes reduction inefficiency, color purity, or durability. Therefore, there is a demandfor a host material having a sufficiently high S₁, and high chemicalstability and carrier injecting/transporting properties.

Moreover, the content of the host compound in the light emitting layerin the organic electroluminescent element of the present invention isnot particularly limited, but from the viewpoint of luminous efficiencyand driving voltage, it is preferably from 15% by mass to 95% by mass,with respect to the total mass of the compounds forming the lightemitting layer. When the light emitting layer includes a plurality ofkinds of host compounds containing the luminescent compound representedby the general formula (1), the content of the luminescent compoundrepresented by the general formula (1) is preferably from 50% by mass to99% by mass, with respect to the total host compounds.

(Other Layers)

The organic electroluminescent element of the present invention mayinclude layers other than the light emitting layer.

Examples of the organic layer other than the light emitting layer whichmay be included in the organic layer include a hole injecting layer, ahole transporting layer, a blocking layer (a hole blocking layer, anexciton blocking layer, and the like), and an electron transportinglayer. Specifically, examples of the layer configuration include thosedescribed below, but it should not be construed that the presentinvention is limited to these configurations.

Anode/hole transporting layer/light emitting layer/electron transportinglayer/cathode,

Anode/hole transporting layer/light emitting layer/blockinglayer/electron transporting layer/cathode,

Anode/hole transporting layer/light emitting layer/blockinglayer/electron transporting layer/electron injecting layer/cathode,

Anode/hole injecting layer/hole transporting layer/light emittinglayer/blocking layer/electron transporting layer/cathode,

Anode/hole injecting layer/hole transporting layer/light emittinglayer/electron transporting layer/electron injecting layer/cathode,

Anode/hole injecting layer/hole transporting layer/light emittinglayer/blocking layer/electron transporting layer/electron injectinglayer/cathode,

Anode/hole injecting layer/hole transporting layer/blocking layer/lightemitting layer/blocking layer/electron transporting layer/electroninjecting layer/cathode.

The organic electroluminescent element of the present inventionpreferably includes at least one (A) organic layer which is preferablydisposed between the anode and the light emitting layer. Examples of the(A) organic layer which is preferably disposed between the anode and thelight emitting layer include an hole injecting layer, a holetransporting layer, and an electron blocking layer from the anode side.

The organic electroluminescent element of the present inventionpreferably includes at least one (B) organic layer which is preferablydisposed between the cathode and the light emitting layer. Examples ofthe (B) organic layer which is preferably disposed between the cathodeand the light emitting layer include an electron injecting layer, anelectron transporting layer, and a hole blocking layer from the cathodeside.

Specifically, an example of the preferred aspects of the organicelectroluminescent element of the present invention is the aspect shownin FIG. 1, in which a hole injecting layer 4, a hole transporting layer5, a light emitting layer 6, a hole blocking layer 7, and an electrontransporting layer 8 are laminated in this order as the organic layerfrom the anode 3 side.

Hereinafter, the layers other than the light emitting layer which theorganic electroluminescent element of the present invention may havewill be described.

(A) Organic Layer Preferably Disposed Between Anode and Light EmittingLayer:

First, the (A) organic layer preferably disposed between the anode andthe light emitting layer will be described.

(A-1) Hole Injecting Layer and Hole Transporting Layer

The hole injecting layer and the hole transporting layer are layershaving a function of receiving holes from the anode or the anode sideand transporting them to the cathode side.

The light emitting element of the present invention preferably includesat least one organic layer between the light emitting layer and theanode, and the organic layer(s) preferably includes at least onecompound of the compounds represented by the following general formulae(Sa-1), (Sb-1), and (Sc-1).

(In the formula, X represents a substituted or unsubstituted alkylenegroup having 1 to 30 carbon atoms, a substituted or unsubstitutedalkenylene group having 2 to 30 carbon atoms, a substituted orunsubstituted arylene group having 6 to 30 carbon atoms, a substitutedor unsubstituted heteroarylene group having 2 to 30 carbon atoms, asubstituted or unsubstituted heterocyclic group having 2 to 30 carbonatoms, or a group formed by a combination thereof. R^(S1), R^(S2), andR^(S3) each independently represent a hydrogen atom, a substituted orunsubstituted alkyl group having 1 to 30 carbon atoms, a substituted orunsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted orunsubstituted aryl group having 6 to 30 carbon atoms, a substituted orunsubstituted aryloxy group having 6 to 30 carbon atoms, a substitutedor unsubstituted heterocyclic group having 2 to 30 carbon atoms, asubstituted or unsubstituted fused polycyclic group having 5 to 30carbon atoms, a hydroxyl group, a cyano group, or a substituted orunsubstituted amino group. Adjacent R^(S1) and R^(S2), and R^(S3) may bebonded to each other to form a saturated carbocycle or an unsaturatedcarbocycle. Ar^(S1) and Ar^(S2) each independently represent asubstituted or unsubstituted aryl group having 6 to 30 carbon atoms, ora substituted or unsubstituted heteroaryl group having 2 to 30 carbonatoms.)

(In the formula, R^(S4), R^(S5), R^(S6), and R^(S7) each independentlyrepresent a hydrogen atom, a substituted or unsubstituted alkyl grouphaving 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy grouphaving 1 to 30 carbon atoms, a substituted or unsubstituted aryl grouphaving 6 to 30 carbon atoms, a substituted or unsubstituted aryloxygroup having 6 to 30 carbon atoms, a substituted or unsubstitutedheterocycle having 2 to 30 carbon atoms, a substituted or unsubstitutedfused polycyclic group having 5 to 30 carbon atoms, a hydroxyl group, acyano group, or a substituted or unsubstituted amino group. AdjacentR^(S4), R^(S5), R^(S6), and R^(S7) may be bonded to each other to form asaturated carbocycle or an unsaturated carbocycle. Ar^(S3) represents asubstituted or unsubstituted aryl group having 6 to 30 carbon atoms, ora substituted or unsubstituted heteroaryl group having 2 to 30 carbonatoms.)

(In the formula, R^(S8) and R^(S9) each independently represent ahydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30carbon atoms, a substituted or unsubstituted aryl group having 6 to 30carbon atoms, a substituted or unsubstituted heterocyclic group having 2to 30 carbon atoms, or a substituted or unsubstituted fused polycyclicgroup having 5 to 30 carbon atoms. R^(S10) represents a substituted orunsubstituted alkyl group having 1 to 30 carbon atoms, a substituted orunsubstituted aryl group having 6 to 30 carbon atoms, a substituted orunsubstituted heterocyclic group having 2 to 30 carbon atoms, or asubstituted or unsubstituted fused polycyclic group having 5 to 30carbon atoms. R^(S11) and R^(S12) each independently represent ahydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30carbon atoms, a substituted or unsubstituted aryl group having 6 to 30carbon atoms, a substituted or unsubstituted aryloxy group having 6 to30 carbon atoms, a substituted or unsubstituted heterocycle having 2 to30 carbon atoms, a substituted or unsubstituted fused polycyclic grouphaving 5 to 30 carbon atoms, a hydroxyl group, a cyano group, or asubstituted or unsubstituted amino group. Adjacent R^(S11) and R^(S12)may be bonded to each other to form a saturated carbocycle or anunsaturated carbocycle. Ar^(S4) represents a substituted orunsubstituted aryl group having 6 to 30 carbon atoms, or a substitutedor unsubstituted heteroaryl group having 2 to 30 carbon atoms. Y^(S1)and Y^(S2) each independently represent a substituted or unsubstitutedalkylene group having 1 to 30 carbon atoms, or a substituted orunsubstituted arylene group having 6 to 30 carbon atoms. n and m eachindependently represent an integer of 0 to 5.)

The general formula (Sa-1) will be described. In the general formula(Sa-1), X represents a substituted or unsubstituted alkylene grouphaving 1 to 30 carbon atoms, a substituted or unsubstituted alkenylenegroup having 2 to 30 carbon atoms, a substituted or unsubstitutedarylene group having 6 to 30 carbon atoms, a substituted orunsubstituted heteroarylene group having 2 to 30 carbon atoms, asubstituted or unsubstituted heterocycle having 2 to 30 carbon atoms, ora group formed by a combination thereof. X is preferably a substitutedor unsubstituted arylene group having 6 to 30 carbon atoms, morepreferably a substituted or unsubstituted phenylene, a substituted orunsubstituted biphenylene, and a substituted or unsubstitutednaphthylene, and still more preferably a substituted or unsubstitutedbiphenylene.

R^(S1), R^(S2), and R^(S3) each independently represent a hydrogen atom,a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, asubstituted or unsubstituted aryloxy group having 6 to 30 carbon atoms,a substituted or unsubstituted heterocycle having 2 to 30 carbon atoms,a substituted or unsubstituted fused polycyclic group having 5 to 30carbon atoms, a hydroxyl group, a cyano group, or a substituted orunsubstituted amino group. Adjacent R^(S1), R^(S2), and R^(S3) may bebonded to each other to form a saturated carbocycle or an unsaturatedcarbocycle. Examples of the saturated carbocycle or the unsaturatedcarbocycle include naphthalene, azulene, anthracene, fluorene, andphenalene. R^(S1), R^(S2), and R^(S3) are preferably a hydrogen atom, asubstituted or unsubstituted alkyl group having 1 to 30 carbon atoms, asubstituted or unsubstituted aryl group having 6 to 30 carbon atoms, asubstituted or unsubstituted fused polycyclic group having 5 to 30carbon atoms, or a cyano group, and more preferably a hydrogen atom.

Ar^(S1) and Ar^(S2) each independently represent a substituted orunsubstituted aryl group having 6 to 30 carbon atoms, or a substitutedor unsubstituted heteroaryl group having 2 to 30 carbon atoms. Ar^(S1)and Ar^(S2) are preferably a substituted or unsubstituted phenyl group.

Next, the general formula (Sb-1) will be described. In the generalformula (Sb-1), R^(S4), R^(S5), R^(S6) and R^(S7) each independentlyrepresent a hydrogen atom, a substituted or unsubstituted alkyl grouphaving 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy grouphaving 1 to 30 carbon atoms, a substituted or unsubstituted aryl grouphaving 6 to 30 carbon atoms, a substituted or unsubstituted aryloxygroup having 6 to 30 carbon atoms, a substituted or unsubstitutedheterocycle having 2 to 30 carbon atoms, or a substituted orunsubstituted fused polycyclic group having 5 to 30 carbon atoms, ahydroxyl group, a cyano group, or a substituted or unsubstituted aminogroup. Adjacent R^(S4), R^(S5), R^(S6) and R^(S7) may be bonded to eachother to form a saturated carbocycle or an unsaturated carbocycle.Examples of the saturated carbocycle or the unsaturated carbocycleinclude naphthalene, azulene, anthracene, fluorene, and phenalene.R^(S4), R^(S5), R^(S6) and R^(S7) are preferably a hydrogen atom, asubstituted or unsubstituted alkyl group having 1 to 30 carbon atoms, asubstituted or unsubstituted aryl group having 6 to 30 carbon atoms, asubstituted or unsubstituted fused polycyclic group having 5 to 30carbon atoms, or a cyano group, and more preferably a hydrogen atom.

Ar^(S3) represents a substituted or unsubstituted aryl group having 6 to30 carbon atoms, or a substituted or unsubstituted heteroaryl grouphaving 2 to 30 carbon atoms. Ar^(S3) is preferably a substituted orunsubstituted phenyl group.

Next, the general formula (Sc-1) will be described. In the generalformula (Sc-1), R^(S8) and R^(S9) each independently represent ahydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30carbon atoms, a substituted or unsubstituted aryl group having 6 to 30carbon atoms, a substituted or unsubstituted heterocyclic group having 2to 30 carbon atoms, or a substituted or unsubstituted fused polycyclicgroup having 5 to 30 carbon atoms. R^(S8) and R^(S9) are preferably asubstituted or unsubstituted alkyl group having 1 to 30 carbon atoms, ora substituted or unsubstituted aryl group having 6 to 30 carbon atoms,and more preferably a methyl group or a phenyl group. R^(S10) is asubstituted or unsubstituted alkyl group having 1 to 30 carbon atoms, asubstituted or unsubstituted aryl group having 6 to 30 carbon atoms, asubstituted or unsubstituted heterocyclic group having 2 to 30 carbonatoms, or a substituted or unsubstituted fused polycyclic group having 5to 30 carbon atoms. R^(S10) is preferably a substituted or unsubstitutedaryl group having 6 to 30 carbon atoms, and more preferably a phenylgroup. R^(S11) and R^(S12) each independently represent a hydrogen atom,a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, asubstituted or unsubstituted aryloxy group having 6 to 30 carbon atoms,a substituted or unsubstituted heterocycle having 2 to 30 carbon atoms,a substituted or unsubstituted fused polycyclic group having 5 to 30carbon atoms, a hydroxyl group, a cyano group, or a substituted orunsubstituted amino group. Adjacent R^(S11) and R^(S12) may be bonded toeach other to form a saturated carbocycle or an unsaturated carbocycle.Examples of the saturated carbocycle or the unsaturated carbocycleinclude naphthalene, azulene, anthracene, fluorene, and phenalene.R^(S11) and R^(S12) are preferably a hydrogen atom, a substituted orunsubstituted alkyl group having 1 to 30 carbon atoms, a substituted orunsubstituted aryl group having 6 to 30 carbon atoms, a substituted orunsubstituted fused polycyclic group having 5 to 30 carbon atoms, or acyano group, and more preferably a hydrogen atom. Ar^(S4) represents asubstituted or unsubstituted aryl group having 6 to 30 carbon atoms, ora substituted or unsubstituted heteroaryl group having 2 to 30 carbonatoms. Y^(S1) and Y^(S2) represent a substituted or unsubstitutedalkylene having 1 to 30 carbon atoms, or substituted or unsubstitutedarylene having 6 to 30 carbon atoms. Y^(S1) and Y^(S2) are preferably asubstituted or unsubstituted arylene having 6 to 30 carbon atoms, andmore preferably a substituted or unsubstituted phenylene. n is aninteger of 0 to 5, preferably 0 to 3, more preferably 0 to 2, and stillmore preferably 0. m is an integer of 0 to 5, preferably 0 to 3, morepreferably 0 to 2, and still more preferably 1.

The general formula (Sa-1) is preferably a compound represented by thefollowing general formula (Sa-2).

(In the formula, R^(S1), R^(S2), and R^(S3) each independently representa hydrogen atom, a substituted or unsubstituted alkyl group having 1 to30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to30 carbon atoms, a substituted or unsubstituted aryl group having 6 to30 carbon atoms, a substituted or unsubstituted aryloxy group having 6to 30 carbon atoms, a substituted or unsubstituted heterocycle having 2to 30 carbon atoms, a substituted or unsubstituted fused polycyclicgroup having 5 to 30 carbon atoms, a hydroxyl group, a cyano group, or asubstituted or unsubstituted amino group. Adjacent R^(S2), R^(S2), andR^(S3) may be bonded to each other to form a saturated carbocycle or anunsaturated carbocycle. Q^(Sa)s each independently represent a hydrogenatom, a cyano group, a fluorine atom, an alkoxy group having 1 to 30carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30carbon atoms, an aryloxy group having 6 to 30 carbon atoms, asubstituted or unsubstituted aryl group having 6 to 30 carbon atoms, asubstituted or unsubstituted heterocycle having 2 to 30 carbon atoms, ora substituted or unsubstituted amino group.)

The general formula (Sa-2) will be described. R^(S1), R^(S2), and R^(S3)have the same definitions as those in the general formula (Sa-1), andtheir preferred ranges are also the same. Q^(Sa)s each independentlyrepresent a hydrogen atom, a cyano group, a fluorine atom, an alkoxygroup having 1 to 30 carbon atoms, a substituted or unsubstituted alkylgroup having 1 to 30 carbon atoms, an aryloxy group having 6 to 30carbon atoms, a substituted or unsubstituted aryl group having 6 to 30carbon atoms, a substituted or unsubstituted heterocycle having 2 to 30carbon atoms, or a substituted or unsubstituted amino group. Q_(Sa) ispreferably a hydrogen atom, a cyano group, a fluorine atom, asubstituted or unsubstituted alkyl group having 1 to 30 carbon atoms, ora substituted or unsubstituted aryl group having 6 to 30 carbon atoms,more preferably a hydrogen atom or a substituted or unsubstituted alkylgroup having 1 to 30 carbon atoms, and still more preferably a hydrogenatom.

The general formula (Sb-1) is preferably a compound represented by thefollowing general formula (Sb-2).

(In the formula, R^(S4), R^(S5), R^(S6), and R^(S7) each independentlyrepresent a hydrogen atom, a substituted or unsubstituted alkyl grouphaving 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy grouphaving 1 to 30 carbon atoms, a substituted or unsubstituted aryl grouphaving 6 to 30 carbon atoms, a substituted or unsubstituted aryloxygroup having 6 to 30 carbon atoms, a substituted or unsubstitutedheterocycle having 2 to 30 carbon atoms, a substituted or unsubstitutedfused polycyclic group having 5 to 30 carbon atoms, a hydroxyl group, acyano group, or a substituted or unsubstituted amino group. AdjacentR^(S4), R^(S5), R^(S6) and R^(S7) may be bonded to each other to form asaturated carbocycle or an unsaturated carbocycle. Q^(Sb) represents ahydrogen atom, a cyano group, a fluorine atom, an alkoxy group having 1to 30 carbon atoms, a substituted or unsubstituted alkyl group having 1to 30 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, asubstituted or unsubstituted aryl group having 6 to 30 carbon atoms, asubstituted or unsubstituted heterocycle having 2 to 30 carbon atoms, ora substituted or unsubstituted amino group.)

The general formula (Sb-2) will be described. R^(S4), R^(S5), R^(S6) andR^(S7) have the same definitions as those in the general formula (Sb-1),and their preferred ranges are also the same. Q^(Sa) represents ahydrogen atom, a cyano group, a fluorine atom, an alkoxy group having 1to 30 carbon atoms, a substituted or unsubstituted alkyl group having 1to 30 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, asubstituted or unsubstituted aryl group having 6 to 30 carbon atoms, asubstituted or unsubstituted heterocycle having 2 to 30 carbon atoms, ora substituted or unsubstituted amino group. Q^(Sa) is preferably ahydrogen atom, a cyano group, a fluorine atom, a substituted orunsubstituted alkyl group having 1 to 30 carbon atoms, or a substitutedor unsubstituted aryl group having 6 to 30 carbon atoms, more preferablya hydrogen atom, or a substituted or unsubstituted alkyl group having 1to 30 carbon atoms, and still more preferably a hydrogen atom.

The general formula (Sc-1) is preferably a compound represented by thefollowing general formula (Sc-2).

(In the formula, R^(S8) and R^(S9) each independently represent ahydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30carbon atoms, a substituted or unsubstituted aryl group having 6 to 30carbon atoms, a substituted or unsubstituted heterocyclic group having 2to 30 carbon atoms, or a substituted or unsubstituted fused polycyclicgroup having to 30 carbon atoms. R^(S10) represents a substituted orunsubstituted alkyl group having 1 to 30 carbon atoms, a substituted orunsubstituted aryl group having 6 to 30 carbon atoms, a substituted orunsubstituted heterocyclic group having 2 to 30 carbon atoms, or asubstituted or unsubstituted fused polycyclic group having 5 to 30carbon atoms. R^(S11) and R^(S12) each independently represent ahydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30carbon atoms, a substituted or unsubstituted aryl group having 6 to 30carbon atoms, a substituted or unsubstituted aryloxy group having 6 to30 carbon atoms, a substituted or unsubstituted heterocycle having 2 to30 carbon atoms, or a substituted or unsubstituted fused polycyclicgroup having 5 to 30 carbon atoms, a hydroxyl group, a cyano group, or asubstituted or unsubstituted amino group. Adjacent R^(S11) and R^(S12)may be bonded to each other to form a saturated carbocycle or anunsaturated carbocycle. Q^(Sc) represents a hydrogen atom, a cyanogroup, a fluorine atom, an alkoxy group having 1 to 30 carbon atoms, asubstituted or unsubstituted alkyl group having 1 to 30 carbon atoms, anaryloxy group having 6 to 30 carbon atoms, a substituted orunsubstituted aryl group having 6 to 30 carbon atoms, a substituted orunsubstituted heterocycle having 2 to 30 carbon atoms, or a substitutedor unsubstituted amino group.)

The general formula (Sc-2) will be described. R^(S8), R^(S9), R^(S10),R^(S11) and R^(S12) have the same definitions as those in the generalformula (Sc-1), and their preferred ranges are also the same. Q^(Sc)represents a hydrogen atom, a cyano group, a fluorine atom, an alkoxygroup having 1 to 30 carbon atoms, a substituted or unsubstituted alkylgroup having 1 to 30 carbon atoms, an aryloxy group having 6 to 30carbon atoms, a substituted or unsubstituted aryl group having 6 to 30carbon atoms, a substituted or unsubstituted heterocycle having 2 to 30carbon atoms, or a substituted or unsubstituted amino group. Q^(Sc) ispreferably a hydrogen atom, a cyano group, a fluorine atom, asubstituted or unsubstituted alkyl group having 1 to 30 carbon atoms, ora substituted or unsubstituted aryl group having 6 to 30 carbon atoms,more preferably a hydrogen atom, or a substituted or unsubstituted arylgroup having 6 to 30 carbon atoms, and still more preferably a phenylgroup.

Specific examples of the compounds represented by the general formulae(Sa-1), (Sb-1), and (Sc-1) include the following ones. However, thepresent invention is not limited to the following specific examples.

The compound represented by the general formula (Sa-1), (Sb-1), or(Sc-1) can be synthesized by the method described in JP-A-2007-318101.After the synthesis, purification is preferably carried out by columnchromatography, recrystallization, reprecipitation, or the like, andthen by sublimation purification. By the sublimation purification,organic impurities can be separated and inorganic salts, residualsolvents, moisture, or the like can be removed effectively.

In the light emitting element of the present invention, the compoundrepresented by the general formula (Sa-1), (Sb-1), or (Sc-1) ispreferably contained in the organic layer between the light emittinglayer and the anode, and above all, it is more preferably contained inthe layer on the anode side adjacent to the light emitting layer, and itis particularly preferably a hole transporting material contained in thehole transporting layer.

The compound represented by the general formula (Sa-1), (Sb-1), or(Sc-1) is contained in the amount of preferably from 70% by mass to 100%by mass, and more preferably from 85% by mass to 100% by mass, withrespect to the total mass of the organic layer added.

[Compound Represented by General Formula (M-3)]

The organic electroluminescent element of the present invention is amaterial which is particularly preferably used in the (A) organic layerpreferably disposed between the anode and the light emitting layer, andexamples thereof include at least one kind of compound represented bythe following general formula (M-3).

The compound represented by the general formula (M-3) is more preferablycontained in the organic layer adjacent to the light emitting layerbetween the light emitting layer and the anode, but is not limited inits uses and may be further contained in any layer in the organiclayers. A layer into which the compound represented by the generalformula (M-3) is introduced may contain any one or a plurality of alight emitting layer, a hole injecting layer, a hole transporting layer,an electron transporting layer, an electron injecting layer, and acharge blocking layer.

The organic layer adjacent to the light emitting layer between the lightemitting layer and the anode, in which the compound represented by thegeneral formula (M-3) is contained, is more preferably an electronblocking layer or a hole transporting layer.

In the general formula (M-3), R^(S1) to R^(S5) each independentlyrepresent an alkyl group, a cycloalkyl group, an alkenyl group, analkynyl group, —CN, a perfluoroalkyl group, a trifluorovinyl group,—CO₂R, —C(O)R, —NR², —NO₂, —OR, a halogen atom, an aryl group, or aheteroaryl group, and may further have a substituent Z. Rs eachindependently represent a hydrogen atom, an alkyl group, a perhaloalkylgroup, an alkenyl group, an alkynyl group, a heteroalkyl group, an arylgroup, or a heteroaryl group. When a plurality of R^(S1) to R^(S5) arepresent, those groups may be bonded to each other to form a ring, andmay further have a substituent Z.

a represents an integer of 0 to 4, and when a plurality of R^(S1)s arepresent, the R^(S1)s may be the same as or different from one another,and may be bonded to each other to form a ring. b to e eachindependently represent an integer of 0 to 5, and when a plurality ofgroups are present for each R^(S2) to R^(S5), the groups may be the sameas or different from one another, and any two thereof may be bonded toeach other to form a ring.

q is an integer of 1 to 5, and when q is 2 or more, a plurality ofR^(S1)s may be the same as or different from one another and may bebonded to each other to form a ring.

The alkyl group may have a substituent and may be saturated orunsaturated, and examples of the group that may be substituted includethe substituent Zs as described above. The alkyl group represented byR^(S1) to R^(S5) is preferably an alkyl group having a total carbonnumber of 1 to 8, and more preferably an alkyl group having a totalcarbon number of 1 to 6, and examples thereof include a methyl group, anethyl group, an i-propyl group, a cyclohexyl group, and a t-butyl group.

The cycloalkyl group may have a substituent and may be saturated orunsaturated, and examples of the group that may be substituted includethe substituent Zs as described above. The cycloalkyl group representedby R^(S1) to R^(S5) is preferably a cycloalkyl group having 4 to 7 ringmembers, and more preferably a cycloalkyl group having a total carbonnumber of 5 or 6, and examples thereof include a cyclopenthyl group anda cyclohexyl group.

The alkenyl group represented by R^(S1) to R^(S5) preferably has 2 to 30carbon atoms, more preferably has 2 to 20 carbon atoms, and particularlypreferably has 2 to 10 carbon atoms, and examples thereof include vinyl,allyl, 1-propenyl, 1-isopropenyl, 1-butenyl, 2-butenyl, and 3-pentenyl.

The alkynyl group represented by R^(S1) to R^(S5) preferably has 2 to 30carbon atoms, more preferably has 2 to 20 carbon atoms, and particularlypreferably has 2 to 10 carbon atoms, and examples thereof includeethynyl, propargyl, 1-propynyl, and 3-pentynyl.

The perfluoroalkyl group represented by R^(S1) to R^(S5) includes agroup obtained by substituting all the hydrogen atoms in theabove-mentioned alkyl group with fluorine atoms.

The aryl group represented by R^(S1) to R^(S5) is preferably asubstituted or unsubstituted aryl group having 6 to 30 carbon atoms, andexamples thereof include a phenyl group, a tolyl group, a biphenylgroup, and a terphenyl group.

The heteroaryl group represented by R^(S1) to R^(S5) is preferably aheteroaryl group having 5 to 8 carbon atoms, and more preferably asubstituted or unsubstituted 5- or 6-membered heteroaryl group, andexamples thereof include a pyridyl group, a pyrazinyl group, apyridazinyl group, a pyrimidinyl group, a triazinyl group, a quinolinylgroup, an isoquinolinyl group, a quinazolinyl group, a cinnolinyl group,a phthalazinyl group, a quinoxalinyl group, a pyrrolyl group, an indolylgroup, a furyl group, a benzofuryl group, a thienyl group, abenzothienyl group, a pyrazolyl group, an imidazolyl group, abenzimidazolyl group, a triazolyl group, an oxazolyl group, abenzoxazolyl group, a thiazolyl group, a benzothiazolyl group, anisothiazolyl group, a benzisothiazolyl group, a thiadiazolyl group, anisoxazolyl group, a benzisoxazolyl group, a pyrrolidinyl group, apiperidinyl group, a piperazinyl group, an imidazolidinyl group, athiazolinyl group, a sulfolanyl group, a carbazolyl group, adibenzofuryl group, a dibenzothienyl group, and a pyridoindolyl group.Preferred examples thereof include a pyridyl group, a pyrimidinyl group,an imidazolyl group, and a thienyl group, and more preferred examplesthereof include a pyridyl group and a pyrimidinyl group.

R^(S1) to R^(S5) are each preferably a hydrogen atom, an alkyl group, acyano group, a trifluoromethyl group, a perfluoroalkyl group, adialkylamino group, a fluoro group, an aryl group, or a heteroarylgroup, more preferably a hydrogen atom, an alkyl group, a cyano group, atrifluoromethyl group, a fluoro group, or an aryl group, and still morepreferably a hydrogen atom, an alkyl group, or an aryl group. Thesubstituent Z is preferably an alkyl group, an alkoxy group, a fluorogroup, a cyano group, or a dialkylamino group, and more preferably ahydrogen atom or an alkyl group.

Any two of R^(S1) to R^(S5) may be bonded to each other to form a fused4- to 7-membered ring, the fused 4- to 7-membered ring is cycloalkyl,aryl, or heteroaryl, and the fused 4- to 7-membered ring may furtherhave a substituent Z. The definitions and the preferred ranges of theformed cycloalkyl, aryl and heteroaryl are the same as those of thecycloalkyl group, the aryl group, and the heteroaryl group defined inR^(S1) to R^(S5).

In the case where the compound represented by the general formula (M-3)is used in a hole transporting layer, the compound represented by thegeneral formula (M-3) is preferably contained in an amount of 50% bymass to 100% by mass, more preferably contained in an amount of 80% bymass to 100% by mass, and particularly preferably contained in an amountof 95% by mass to 100% by mass.

In addition, in the case where the compound represented by the generalformula (M-3) is used in a plurality of organic layers, the compound ispreferably contained in each layer within the above range.

The thickness of the hole transporting layer containing the compoundrepresented by the general formula (M-3) is preferably from 1 nm to 500nm, more preferably from 3 nm to 200 nm, and still more preferably from5 nm to 100 nm. In addition, the hole transporting layer is preferablyprovided to be adjacent to the light emitting layer.

Specific examples of the compound represented by the general formula(M-3) are shown below, but the present invention is not limited thereto.

In addition, with respect to the hole injecting layer and the holetransporting layer, the detailed descriptions in paragraph Nos. [0165]to [0167] of JP-A-2008-270736 can be applied to the present invention.Further, the detailed descriptions in paragraph Nos. [0250] to [0339] ofJP-A-2011-71452 can be applied to the hole injecting layer and the holetransporting layer of the present invention.

The hole injecting layer preferably contains an electron receptivedopant. By incorporating the electron receptive dopant in the holeinjecting layer, there are effects in which, for example, the holeinjecting properties are improved, the driving voltage is lowered, andthe efficiency is improved. The electron receptive dopant may be any oneof organic materials and inorganic materials as long as it is capable ofwithdrawing electrons from a material to be doped and generating radicalcations, and examples thereof include TCNQ compounds such astetracyanoquinodimethane (TCNQ) and tetrafluorotetracyanoquinodimethane(F₄-TCNQ), hexaazatriphenylene compounds such ashexacyanohexaazatriphenylene (HAT-CN), and molybdenum oxide.

The electron receptive dopant in the hole injecting layer is containedin the amount of preferably from 0.01% by mass to 50% by mass, morepreferably from 0.1% by mass to 40% by mass, and still more preferablyfrom 0.2% by mass to 30% by mass, with respect to the total mass of thecompounds forming the hole injecting layer.

(A-2) Electron Blocking Layer

The electron blocking layer is a layer having a function of preventingthe electrons, which have been transported from the cathode side to thelight emitting layer, from passing through to the anode side. In thepresent invention, the electron blocking layer can be provided as anorganic layer adjacent to the light emitting layer on the anode side.

As the organic compound constituting the electron blocking layer, forexample, those exemplified above as the hole transporting material canbe applied.

The thickness of the electron blocking layer is preferably from 1 nm to500 nm, more preferably from 3 nm to 100 nm, and still more preferablyfrom 5 nm to 50 nm.

The electron blocking layer may have either a single layer structurecomposed of one kind or two or more kinds of materials selected from theabove-exemplified materials or a multilayer structure composed of aplurality of layers having the same composition or differentcompositions.

The material used in the electron blocking layer preferably has higherS₁ energy than that of the light emitting material from the viewpointsof color purity, luminous efficiency, and driving durability. The S₁ inthe film state of the material used in the electron blocking layer ishigher than the S₁ of the light emitting material preferably by 0.1 eVor more, more preferably by 0.2 eV or more, and still more preferably by0.3 eV or more.

(B) Organic Layer Preferably Disposed between Cathode and Light EmittingLayer

Next, the (B) organic layer preferably disposed between the cathode andthe light emitting layer will be described.

(B-1) Electron Injecting Layer and Electron Transporting Layer

The electron injecting layer and the electron transporting layer arelayers having a function of receiving electrons from the cathode or thecathode side and transporting them to the anode side. The electroninjecting material and the electron transporting material used in theselayers may be either a low-molecular compound or a high-molecularcompound.

As the electron transporting material, for example, the luminescentcompound represented by the general formula (1) can be used. As theother electron transporting materials, any one selected from aromaticring tetracarboxylic acid anhydrides, such as pyridine derivatives,quinoline derivatives, pyrimidine derivatives, pyrazine derivatives,phthalazine derivatives, phenanthroline derivatives, triazinederivatives, triazole derivatives, oxazole derivatives, oxadiazolederivatives, imidazole derivatives, benzimidazole derivatives,imidazopyridine derivatives, fluorenone derivatives,anthraquinodimethane derivatives, anthrone derivatives, diphenylquinonederivatives, thiopyranedioxide derivatives, carbodiimide derivatives,fluorenylidenemethane derivatives, distyrylpyrazine derivatives,naphthalene, and perylene; various metal complexes typified by metalcomplexes of phthalocyanine derivatives or 8-quinolinol derivatives andmetal complexes having metal phthalocyanine, benzoxazole, orbenzothiazole as a ligand thereof; organic silane derivatives typifiedby silole; and hydrocarbon compounds with fused rings, such asnaphthalene, anthracene, phenanthrene, triphenylene, and pyrene ispreferred, and any one selected from pyridine derivatives, benzimidazolederivatives, imidazopyridine derivatives, metal complexes, andhydrocarbon compounds with fused rings is more preferred.

From the viewpoint of decreasing the driving voltage, the thickness ofeach of the electron injecting layer and the electron transporting layeris preferably 500 nm or less.

The thickness of the electron transporting layer is preferably from 1 nmto 500 nm, more preferably from 5 nm to 200 nm, and still morepreferably from 10 nm to 100 nm. In addition, the thickness of theelectron injecting layer is preferably from 0.1 nm to 200 nm, morepreferably from 0.2 nm to 100 nm, and still more preferably from 0.5 nmto 50 nm. The electron injecting layer and the electron transportinglayer may have either a single layer structure composed of one kind ortwo or more kinds of the above-described materials or a multilayerstructure composed of a plurality of layers having the same compositionor different compositions.

The electron injecting layer preferably contains an electron donatingdopant. By incorporating the electron donating dopant in the electroninjecting layer, there are effects that, for example, the electroninjecting properties are improved, the driving voltage is lowered, andthe efficiency is improved. The electron donating dopant may be any oneof organic materials and inorganic materials as long as it is capable ofgiving electrons to the material to be doped and generating radicalanions, and examples thereof include dihydroimidazole compounds such astetrathiafulvalene (TTF), tetrathianaphthacene (TTT), andbis-[1,3-diethyl-2-methyl-1,2-dihydrobenzimidazolyl], lithium, andcesium.

The electron donating dopant in the electron injecting layer iscontained in the amount of preferably from 0.01% by mass to 50% by mass,more preferably from 0.1% by mass to 40% by mass, and still morepreferably 0.5% by mass to 30% by mass, with respect to the total massof the compounds forming the electron injecting layer.

(B-2) Hole Blocking Layer

The hole blocking layer is a layer having a function of preventingholes, which have been transported from the anode side to the lightemitting layer, from passing through to the cathode side. In the presentinvention, the hole blocking layer can be provided as an organic layeradjacent to the light emitting layer on the cathode side.

In order that the S₁ energy of the organic compound in the film stateconstituting the hole blocking layer prevents the energy movement ofexcitons produced in the light emitting layer, and thus, does not lowerthe luminous efficiency, it is preferably higher than S₁ energy of thelight emitting material.

As an example of the organic compound constituting the hole blockinglayer, for example, the luminescent compound represented by the generalformula (1) can be used.

Examples of the organic compounds constituting the hole blocking layer,other than the luminescent compound represented by the general formula(1), include aluminum complexes such as aluminum (III)bis(2-methyl-8-quinolinato)-4-phenylphenolate (abbreviated as BAlq),triazole derivatives, and phenanthroline derivatives such as2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (abbreviated as BCP).

The thickness of the hole blocking layer is preferably from 1 nm to 500nm, more preferably from 3 nm to 100 nm, and still more preferably from5 nm to 50 nm.

The hole blocking layer may have either a single layer structurecomposed of one kind or two or more kinds of the above-describedmaterials or a multilayer structure composed of a plurality of layershaving the same composition or different compositions.

The material used in the hole blocking layer preferably has higher S₁energy than that of the light emitting material from the viewpoints ofcolor purity, luminous efficiency, and driving durability. The S₁ in thefilm state of the material used in the hole blocking layer is preferablyhigher than the S₁ of the light emitting material by 0.1 eV or more,more preferably by 0.2 eV or more, and still more preferably by 0.3 eVor more.

(B-3) Material which is Particularly Preferably Used in Organic Layer,Preferably Disposed between Cathode and Light Emitting Layer

For the organic electroluminescent element of the present invention,examples of the material which is particularly preferably used in the(B) materials for an organic layer, preferably disposed between thecathode and the light emitting layer include the luminescent compoundrepresented by the general formula (1), a compound represented by thefollowing general formula (P-1), and a compound represented by thefollowing general formula (O-1).

Hereinafter, a compound represented by the general formula (O-1) and acompound represented by the general formula (P-1) will be described.

The organic electroluminescent element of the present inventionpreferably includes at least one organic layer between the lightemitting layer and the cathode, and the organic layer preferablycontains at least one of compounds represented by the following generalformula (O-1), from the viewpoint of efficiency or driving voltage of anelement. Hereinafter, the general formula (O-1) will be described.

(In the general formula (O-1), R^(O1) represents an alkyl group, an arylgroup, or a heteroaryl group. A^(O1) to A^(O4) each independentlyrepresent C—R^(A) or a nitrogen atom. R^(A) represents a hydrogen atom,an alkyl group, an aryl group, or a heteroaryl group, and a plurality ofR^(A)s may be the same as or different from each other. L^(O1)represents any of divalent to hexavalent linking groups with an arylring or a heteroaryl ring. n^(O1) represents an integer of 2 to 6).

R^(O1) represents an alkyl group (preferably having 1 to 8 carbonatoms), an aryl group (preferably having 6 to 30 carbon atoms), or aheteroaryl group (preferably having 4 to 12 carbon atoms), which mayhave a substituent selected from the Substituent Group A as describedabove. R^(O1) is preferably an aryl group or a heteroaryl group, andmore preferably an aryl group. Preferred examples of the substituent inthe case where the aryl group of R^(O1) has a substituent include analkyl group, an aryl group, and a cyano group, more preferred examplesthereof include an alkyl group and an aryl group, and still morepreferred examples thereof include an aryl group. In the case where thearyl group of R^(O1) has a plurality of substituents, the plurality ofsubstituents may be bonded to each other to form a 5- or 6-memberedring. The aryl group of R^(O1) is preferably a phenyl group which mayhave a substituent selected from Substituent Group A, more preferably aphenyl group which may be substituted with an alkyl group or an arylgroup, and still more preferably an unsubstituted phenyl group or2-phenylphenyl group.

A^(O1) to A^(O4) each independently represent C—R^(A) or a nitrogenatom. It is preferable that 0 to 2 groups out of A^(O1) to A^(O4) benitrogen atoms; and it is more preferable that 0 or 1 group out ofA^(O1) to A^(O4) be nitrogen atoms. It is preferable that all of A^(O1)to A^(O4) be C—R^(A), or A^(O1) be a nitrogen atom, and A^(O2) to A^(O4)be C—R^(A); it is more preferable that A^(O1) be a nitrogen atom, andA^(O2) to A^(O4) be C—R^(A); and it is still more preferable that A^(O1)be a nitrogen atom, A^(O2) to A^(O4) be C—R^(A), and R^(A)s be allhydrogen atoms.

R^(A) represents a hydrogen atom, an alkyl group (preferably having 1 to8 carbon atoms), an aryl group (preferably having 6 to 30 carbon atoms),or a heteroaryl group (preferably having 4 to 12 carbon atoms), whichmay have a substituent selected from the Substituent Group A asdescribed above. Further, a plurality of R^(A)s may be the same as ordifferent from each other. R^(A) is preferably a hydrogen atom or analkyl group, and more preferably a hydrogen atom.

L^(O1) represents any of a divalent to hexavalent linking groupincluding an aryl ring (preferably having 6 to 30 carbon atoms) or aheteroaryl ring (preferably having 4 to 12 carbon atoms). L^(O1) ispreferably an arylene group, a heteroarylene group, an aryltriyl group,or a heteroaryltriyl group, more preferably a phenylene group, abiphenylene group, or a benzenetriyl group, and still more preferably abiphenylene group or a benzenetriyl group. L^(O1) may have a substituentselected from the Substituent Group A as described above, and in a caseof having the substituent, the substituent is preferably an alkyl group,an aryl group, or a cyano group. Specific examples of L^(O1) include thefollowing.

n^(O1) represents an integer of 2 to 6, preferably an integer of 2 to 4,and more preferably 2 or 3. n^(O1) is most preferably 3 from theviewpoint of the efficiency of an element, or most preferably 2 from theviewpoint of the durability of an element.

The glass transition temperature (Tg) of the compound represented by thegeneral formula (O-1) is preferably from 100° C. to 300° C., morepreferably from 120° C. to 300° C., still more preferably from 120° C.to 300° C., and even still more preferably from 140° C. to 300° C., fromthe viewpoint of stability at the time of storage at a high temperature,or stable operation during driving at a high temperature or against heatgeneration during driving.

Specific examples of the compound represented by the general formula(O-1) are shown below, but the compound represented by the generalformula (O-1), which can be used in the present invention, should not beconstrued to be limited to the specific examples.

The compound represented by the general formula (O-1) can be synthesizedby the method described in JP-A-2001-335776. After the synthesis,purification is preferably carried out by column chromatography,recrystallization, reprecipitation, or the like, and then by sublimationpurification. By the sublimation purification, organic impurities can beseparated and inorganic salts, residual solvents, moisture, or the likecan be removed effectively.

In the organic electroluminescent element of the present invention, thecompound represented by the general formula (O-1) is preferablycontained in the organic layer between the light emitting layer and thecathode, however, it is more preferably contained in the layer on thecathode side adjacent to the light emitting layer.

The compound represented by the general formula (O-1) is contained inthe amount of preferably from 70% by mass to 100% by mass, and morepreferably from 85% by mass to 100% by mass, with respect to the totalmass of the organic layer added.

The organic electroluminescent element of the present inventionpreferably includes at least one layer of organic layers between thelight emitting layer and the cathode, and it is preferable that theorganic layer contain at least one of compounds represented by thefollowing general formula (P), from the viewpoint of efficiency or thedriving voltage of an element. Hereinafter, the general formula (P) willbe described.

(In the general formula (P), R^(P) represents an alkyl group (preferablyhaving 1 to 8 carbon atoms), an aryl group (preferably having 6 to 30carbon atoms), or a heteroaryl group (preferably having 4 to 12 carbonatoms), which may have a substituent selected from the Substituent GroupA as described above. nP represents an integer of 1 to 10, and in thecase where there are a plurality of R^(P)s, these may be the same as ordifferent from each other. At least one of R^(P)s is a substituentrepresented by the following general formulae (P-1) to (P-3).

(In the general formulae (P-1) to (P-3), R^(P1) to R^(P3) and R′^(P1) toR′^(P3) each represent an alkyl group (preferably having 1 to 8 carbonatoms), an aryl group (preferably having 6 to 30 carbon atoms), or aheteroaryl group (preferably having 4 to 12 carbon atoms), which mayhave a substituent selected from the Substituent Group A as describedabove. n^(P1) to n^(P2) each represent an integer of 0 to 4, and in thecase where there are a plurality of R^(P1) to R^(P3) and R′^(P1) toR′^(P3), they may be the same as or different from each other. L^(P1) toL^(P3) represents any one of divalent linking groups consisting of asingle bond, an aryl ring, and a heteroaryl ring. * represents a bindingposition with the anthracene ring of the general formula (P).)

A preferred substituent other than the substituents represented by (P-1)to (P-3) as R^(P) is an aryl group, more preferred substituent is anyone of a phenyl group, a biphenyl group, a terphenyl group, and anaphthyl group, and still more preferred substituent is a naphthylgroup.

R^(P1) to R^(P3) and R′^(P1) to R′^(P3) are preferably any one of anaryl group and a heteroaryl group, more preferably an aryl group, stillmore preferably any one of a phenyl group, a biphenyl group, a terphenylgroup, and a naphthyl group, and most preferably a phenyl group.

L^(P1) to L^(P3) are preferably any one of divalent linking groupsconsisting of a single bond and an aryl ring, more preferably any one ofa single bond, phenylene, biphenylene, terphenylene, and naphthylene,and still more preferably any one of a single bond, phenylene, andnaphthylene.

Specific examples of the compound represented by the general formula (P)are shown below, but it should not construed that the compoundrepresented by the general formula (P) that can be used in the presentinvention is limited to the specific examples.

The compound represented by the general formula (P) can be synthesizedby the method described in WO 2003/060956 and WO 2004/080975. After thesynthesis, purification is preferably carried out by columnchromatography, recrystallization, reprecipitation, or the like, andthen by sublimation purification. By the sublimation purification,organic impurities can be separated and inorganic salts, residualsolvents, moisture, or the like can be removed effectively.

In the organic electroluminescent element of the present invention, thecompound represented by the general formula (P) is preferably containedin the organic layer between the light emitting layer and the cathode,and more preferably contained in the layer adjacent to the cathode.

The compound represented by the general formula (P) is contained in theamount of preferably from 70% by mass to 100% by mass, and morepreferably from 85% by mass to 100% by mass, with respect to the totalmass of the organic layer added.

Preferred examples of the other material used in the electron injectinglayer or the electron transporting layer in the organicelectroluminescent element of the present invention include silolecompounds described in JP-A-09-194487 or the like, phosphineoxidecompounds described in JP-A-2006-73581 or the like, nitrogen-containingaromatic 6-membered ring hetero compounds described in JP-A-2005-276801,JP-A-2006-225320, WO 2005/085387, or the like, compounds havingnitrogen-containing aromatic 6-membered hetero structures and carbazolestructures, described in WO 2003/080760, WO 2005/085387, or the like,and aromatic hydrocarbon compounds described in US2009/0009065, WO2010/134350, JP-T-2010-535806, or the like (naphthalene compounds,anthracene compounds, triphenylene compounds, phenanthrene compounds,pyrene compounds, fluoranthene compounds, and the like).

<Protective Layer>

In the present invention, the entirety of the organic electroluminescentelement may be protected by a protective layer.

For the protective layer, the detailed descriptions in paragraph Nos.[0169] to [0170] of JP-A-2008-270736 can be applied to the presentinvention. Incidentally, the materials for the protective layer may beeither an inorganic material or an organic material.

<Sealing Enclosure>

For the organic electroluminescent element according to the presentinvention, the entirety of the element may be sealed using a sealingenclosure.

For the sealing enclosure, the detailed description in paragraph No.[0171] of JP-A-2008-270736 can be applied to the present invention.

<Driving Method>

The organic electroluminescent element of the present invention can emitlight by applying a direct current (it may contain an alternate currentcomponent, if necessary) voltage (typically from 2 volts to 15 volts) ora direct current between the anode and the cathode.

As a driving method of the organic electroluminescent element of thepresent invention, driving methods described in each of the publicationsof JP-A-2-148687, JP-A-6-301355, JP-A-5-29080, JP-A-7-134558,JP-A-8-234685, and JP-A-8-241047, Japanese Patent No. 2784615, and U.S.Pat. Nos. 5,828,429 and 6,023,308 can be applied.

The external quantum efficiency of the organic electroluminescentelement of the present invention is preferably 5% or more, morepreferably 6% or more, and still more preferably 7% or more. As to thenumerical value of the external quantum efficiency, a maximum value ofthe external quantum efficiency obtained when the organicelectroluminescent element is driven at 20° C., or a value of theexternal quantum efficiency in the vicinity of from 300 cd/m² to 400cd/m² obtained when the element is driven at 20° C. can be employed.

The internal quantum efficiency of the organic electroluminescentelement of the present invention is preferably 30% or more, morepreferably 50% or more, and still more preferably 70% or more. Theinternal quantum efficiency of the element is calculated by dividing theexternal quantum efficiency by the light extraction efficiency. Thelight extraction efficiency in usual organic EL elements is about 20%,but by adjusting the shape of a substrate, the shape of an electrode,the thickness of an organic layer, the thickness of an inorganic layer,the refractive index of an organic layer, the refractive index of aninorganic layer, or the like, it is possible to increase the lightextraction efficiency to 20% or more.

<Light Emitting Wavelength>

In the organic electroluminescent element of the present invention, itslight emitting wavelength is not limited, but is preferably used forblue or white light emission. Above all, in the organicelectroluminescent element of the present invention, the luminescentcompound represented by the general formula (1) is preferably used as alight emitting material to emit fluorescent light, and particularlypreferably to emit blue light.

<Use of Organic Electroluminescent element of the Present Invention>

The organic electroluminescent element of the present invention can besuitably used for display elements, displays, backlights,electrophotography, illumination light sources, recording light sources,exposure light sources, readout light sources, signs, billboards,interior decorations, optical communications, and the like, andparticularly preferably for devices driven in a region of high-intensityluminescence, such as a light emitting device, an illumination device,and a display device.

[Light Emitting Device]

The light emitting device of the present invention includes the organicelectroluminescent element of the present invention.

Next, the light emitting device of the present invention will bedescribed with reference to FIG. 2.

The light emitting device of the present invention is formed by usingthe organic electroluminescent element.

FIG. 2 is a cross-sectional view schematically showing one example ofthe light emitting device of the present invention. The light emittingdevice 20 in FIG. 2 includes a transparent substrate 2 (supportingsubstrate), an organic electroluminescent element 10, a sealingenclosure 16, and the like.

The organic electroluminescent element 10 is formed by laminating on thesubstrate 2 an anode 3 (first electrode), an organic layer 11, and acathode 9 (second electrode) in this order. In addition, a protectivelayer 12 is laminated on the cathode 9, and the sealing enclosure 16 isfurther provided via an adhesive layer 14 on the protective layer 12.Incidentally, a part of each of the electrodes 3 and 9, a diaphragm, aninsulating layer, and the like are omitted.

Here, a photocurable adhesive such as an epoxy resin, or a thermosettingadhesive can be used for the adhesive layer 14, and for example, athermosetting adhesive sheet may also be used.

The light emitting device of the present invention is not particularlylimited in its use, and it can be used as not only an illuminationdevice but also a display device of a television set, a personalcomputer, a mobile phone, electronic paper, or the like.

[Illumination Device]

The illumination device of the present invention includes the organicelectroluminescent element of the present invention.

Next, the illumination device of the present invention will be describedwith reference to FIG. 3.

FIG. 3 is a cross-sectional view schematically showing one example ofthe illumination device of the present invention. The illuminationdevice 40 of the present invention includes, as shown in FIG. 3, theabove-described organic EL element 10 and a light scattering member 30.More specifically, the illumination device 40 is configured such thatthe substrate 2 of the organic EL element 10 and the light scatteringmember 30 are in contact with each other.

The light scattering member 30 is not particularly limited as long as itcan scatter light, but in FIG. 3, a member obtained by dispersing fineparticles 32 in a transparent substrate 31 is used. Suitable examples ofthe transparent substrate 31 include a glass substrate, and suitableexamples of the fine particles 32 include transparent resin fineparticles. As the glass substrate and the transparent resin fineparticles, a known product can be used for both. In such an illuminationdevice 40, when light emitted from the organic electroluminescentelement 10 is incident on the light incident surface 30A of thescattering member 30, the incident light is scattered by the lightscattering member 30 and the scattered light is output as illuminatinglight from the light output surface 30B.

[Display Device]

The display device of the present invention may include the organicelectroluminescent element of the present invention.

The display device of the present invention may be used for, forexample, a display device of a television set, a personal computer, amobile phone, electronic paper, or the like.

EXAMPLES

Hereinafter, the characteristic features of the present invention aredescribed in more detail with reference to the following Examples andComparative Examples. The materials, use amounts, ratios, treatmentdetails, treatment procedures, and the like shown in the followingExamples can be appropriately modified so far as the gist of the presentinvention is not deviated. Accordingly, it should not be construed thatthe scope of the present invention is limited to the specific examplesshown below.

Example 1 1. Synthesis of Luminescent Compound Represented by GeneralFormula (1)

The luminescent compound represented by the general formula (1) (lightemitting material for an organic electroluminescent element) can besynthesized by a combination of known reactions. Representative examplesof the specific synthesis procedure of the luminescent compoundrepresented by the general formula (1) will be described below.

The light emitting material 1 was synthesized according to the synthesisscheme with reference to the well-known literature. In the scheme, Tfrepresents a trifuryl group and TfO represents —OSO₂CF₃.

After the synthesis, purification was carried out by columnchromatography, recrystallization, or the like, and then by sublimationpurification. By the sublimation purification, organic impurities can beseparated and inorganic salts, residual solvents, or the like can beremoved effectively.

The light emitting materials 13, 17, 26, 32, and 34 used in Exampleswere synthesized by a method similar to that for the light emittingmaterial 1.

The comparative compounds 1 to 3 used as the comparative light emittingmaterials have the following structures. The comparative compound 1 isthe compound described in JP-A-2005-82702, and the comparative compound2 is the compound described in JP-A-05-214334.

The following comparative compounds 1 and 2 were synthesized withreference to the well-known literatures in which each of the compoundsis described. The following comparative compound 3 was synthesized withreference to JP-A-2004-204238.

2. Evaluation of Physical Properties of Materials (a) Evaluation ofChromaticity

The following host material H-5 and each of light emitting materialsdescribed in Table 1 below were deposited on a 25 mm×25 mm×0.7 mm quartzglass substrate by a vacuum deposition method in a mass ratio (93:7),thereby forming a thin film having a film thickness of 50 nm. Theobtained film was irradiated with UV rays of 350 nm to emit light. Theluminous spectrum at a time of light emission was measured using afluorescent spectrophotometer (FP-6300, manufactured by JASCOCorporation) and the chromaticity (x, y) was determined. Based on the yvalues at that time, the chromaticity was evaluated as the following 3grades. The results are shown in Table 1 below.

A 0.04≦y≦0.15

B 0.03≦y<0.04, 0.15<y≦0.20

C y<0.03, 0.20<y

TABLE 1 Chroma- Light emitting material ticity Note  1 A The presentinvention 13 A The present invention 17 A The present invention 26 B Thepresent invention 32 A The present invention 34 A The present inventionComparative compound 1 B Comparative Example Comparative compound 2 CComparative Example Comparative compound 3 C Comparative Example

(b) Evaluation of Heat Resistance

10 mg of each of the light-emitting materials described in Table 2 belowwas vacuum-sealed in a glass tube having an inner diameter of 5 mm and atotal length of 50 mm to prepare a sample tube. The obtained sample tubewas heated at a sublimation temperature of +50° C., as determined bythermogravimetric analysis, for 24 hours and the purity of the samplebefore and after heating was determined by HPLC. At this time, the heatresistance was evaluated as the following 2 grades, based on thedecomposition amount of the sample. The results are shown in Table 2below.

A: Decomposition amount>10%

B: Decomposition amount≦10%

TABLE 2 Heat Light emitting material resistance Note  1 A The presentinvention 17 A The present invention 26 A The present invention 32 A Thepresent invention 34 A The present invention Comparative compound 1 BComparative Example Comparative compound 2 A Comparative ExampleComparative compound 3 A Comparative Example

From Tables 1 and 2 above, it could be seen that the light emittingmaterial for an organic electroluminescent element of the presentinvention has good chromaticity and heat resistance.

Meanwhile, it could also be seen that the number of hydrogen atoms ordeuterium atoms in R¹ to R¹⁴ of the general formula (1) is 6, and thecomparative compound 1 described in JP-A-2005-82702, which has thenumber below the lower limit of the range in the present invention, haspoor heat resistance as a light emitting material for an organicelectroluminescent element.

It could be seen that the number of hydrogen atoms or deuterium atoms inR¹ to R¹⁴ of the general formula (1) is 14, and the comparative compound2 described in JP-A-05-2143334, which has the number above the upperlimit of the range in the present invention has poor chromaticity as alight emitting material for an organic electroluminescent element.

It could be seen that the comparative compound 3 having no skeleton ofthe general formula (1) has poor chromaticity as a light emittingmaterial for an organic electroluminescent element.

<Fabrication and Evaluation of Organic Electroluminescent Elements>

The materials used for the fabrication of organic electroluminescentelements were all subjected to sublimation purification and it wasconfirmed that the purity (absorption intensity area ratio at 254 nm)was 99.9% or more by using high performance liquid chromatography(TSKgel ODS-100Z, manufactured by Tosoh Corporation).

The structures of the materials other than the light emitting materialsused for the fabrication of the organic electroluminescent element ineach of Examples and Comparative Examples are shown below.

Example 2

A 0.5 mm-thick and 2.5 cm square glass substrate (manufactured byGeomatec Co., Ltd., surface resistance: 10Ω/□) having an ITO filmthereon was put in a cleaning container. After ultrasonic cleaning in2-propanol, the glass substrate was subjected to a UV-ozone treatmentfor 30 minutes. The following organic compound layers were depositedsequentially on this transparent anode (ITO film) by a vacuum depositionmethod.

Furthermore, the deposition rates in Examples and Comparative Examplesbelow are 0.1 nm/sec unless otherwise indicated. The deposition rateswere measured using a quartz crystal oscillator. Further, the thicknessof each of the layers below was measured using the quartz crystaloscillator.

First layer: HAT-CN: Film thickness of 10 nm

Second layer: HT-2: Film thickness of 30 nm

Third layer: H-1 and the light emitting material described in Table 3(mass ratio=95:5): Film thickness of 30 nm

Fourth layer: ET-1: Film thickness of 30 nm

1 nm of lithium fluoride and 100 nm of metallic aluminum were depositedin this order thereon, thereby forming a cathode. At this time, apatterned mask (mask having a light emitting area of 2 mm×2 mm) wasplaced on the layer of lithium. fluoride, and the metallic aluminum wasdeposited.

The obtained laminate was put in a glove box purged with a nitrogen gaswithout bringing it into contact with the atmosphere and then sealedwith a sealing can made of glass and an ultraviolet ray-curable adhesive(XNR5516HV, manufactured by Nagase-Chiba, Ltd.), thereby obtainingorganic electroluminescent elements 1-1 to 1-5, and comparative organicelectroluminescent elements 1-1 to 1-3, each having a light emittingarea in a 2 mm×2 mm square. Light emission derived from the lightemitting material was observed in each of the elements. For each of theobtained organic electroluminescent elements, the following tests werecarried out. The results of the evaluation from the viewpoints of theluminous efficiency (external quantum efficiency) and the chromaticityare shown in Table 3 below.

(a) External Quantum Efficiency

Light was emitted by applying a direct current voltage to each of theelements by using a source measure unit 2400 manufactured by KeithleyInstruments Inc., and the luminance was measured using a luminance meter(BM-8 manufactured by Topcon Corporation). The luminous spectrum and thelight emitting wavelength were measured using a spectrum analyzer(PMA-11 manufactured by Hamamatsu Photonics K. K.). Based on thesevalues, the external quantum efficiency (η) at a luminance in thevicinity of 1,000 cd/m² was calculated by using a luminance conversionmethod, and is expressed as a relative value, taking the value of theorganic electroluminescent element 1-1 using the light emitting material1 as 1.0. Larger numeral values are preferable because larger numeralvalues indicate better efficiency.

(b) Chromaticity

From the luminous spectrum at a time of light emission by applying adirect current voltage to each of the organic electroluminescentelements to give a luminance of 1000 cd/m², the chromaticity (x, y) wasdetermined. From the y values at that time, the chromaticity wasevaluated as the following 3 grades.

A 0.04≦y≦0.15

B 0.03≦y<0.04, 0.15<y≦0.20

C y<0.03, 0.20<y

TABLE 3 External Light emitting quantum Chroma- Element No. materialefficiency ticity Note Element 1-1  1 1.0 A The present inventionElement 1-2 13 0.9 A The present invention Element 1-3 17 0.8 A Thepresent invention Element 1-4 32 0.8 A The present invention Element 1-534 1.0 A The present invention Comparative Comparative 0.3 B Comparativeelement 1-1 compound 1 Example Comparative Comparative Host material CComparative element 1-2 compound 2 emits light Example ComparativeComparative 1.0 C Comparative element 1-3 compound 3 Example

Example 3

Organic electroluminescent elements 2-1 to 2-5 and comparative elements2-1 to 2-3 were fabricated in the same manner as in Example 2, exceptthat the layer configurations were changed as follows, and evaluationswere carried out in the same manner as in Example 2. The results areshown in Table 4 below. Further, the external quantum efficiency inTable 4 below is expressed as a relative value, taking the value of theorganic electroluminescent element 2-1 using the light emitting material1 as 1.0.

First layer: HT-4: Film thickness of 50 nm

Second layer: HT-3: Film thickness of 45 nm

Third layer: H-2 and the light emitting material described in Table 4below (mass ratio=95:5): Film thickness of 25 nm

Fourth layer: ET-5: Film thickness of 5 nm

Fifth layer: ET-3: Film thickness of 20 nm

TABLE 4 external Light emitting quantum Chroma- Element No. materialefficiency ticity Note Element 2-1  1 1.0 A The present inventionElement 2-2 13 0.9 A The present invention Element 2-3 17 0.8 A Thepresent invention Element 2-4 32 0.8 A The present invention Element 2-534 1.0 A The present invention Comparative Comparative 0.3 B The presentelement 2-1 compound 1 invention Comparative Comparative Host material CComparative element 2-2 compound 2 emits light Example ComparativeComparative 1.0 C Comparative element 2-3 compound 3 Example

Example 4

Organic electroluminescent elements 3-1 to 3-5 and comparative elements3-1 to 3-3 were fabricated in the same manner as in Example 2, exceptthat the layer configurations were changed as follows, and evaluationswere carried out in the same manner as in Example 2. The results areshown in Table 5 below. Further, the external quantum efficiency inTable 5 below is expressed as a relative value, taking the value of theorganic electroluminescent element 3-1 using the light emitting material1 as 1.0.

First layer: HAT-CN: Film thickness of 10 nm

Second layer: HT-2: Film thickness of 30 nm

Third layer: H-1 and the light emitting material described in Table 5below (mass ratio=95:5): Film thickness of 30 nm

Fourth layer: ET-4: Film thickness of 30 nm

TABLE 5 External Light emitting quantum Chroma- Element No. materialefficiency ticity Note Element 3-1  1 1.0 A The present inventionElement 3-2 13 0.9 A The present invention Element 3-3 17 0.9 A Thepresent invention Element 3-4 32 0.8 A The present invention Element 3-534 1.0 A The present invention Comparative Comparative 0.3 B The presentelement 3-1 compound 1 invention Comparative Comparative Host material CComparative element 3-2 compound 2 emits light Example ComparativeComparative 1.0 C Comparative element 3-3 compound 3 Example

Example 5

Organic electroluminescent elements 4-1 to 4-6 and comparative elements3-1 to 3-3 were fabricated in the same manner as in Example 2, exceptthat the layer configurations were changed as follows, and evaluationswere carried out in the same manner as in Example 2. The results areshown in Table 6 below. Further, the external quantum efficiency inTable 6 below is expressed as a relative value, taking the value of theorganic electroluminescent element 4-1 using the light emitting material1 as 1.0.

First layer: HAT-CN: Film thickness of 10 nm

Second layer: HT-1: Film thickness of 30 nm

Third layer: H-3 and the light emitting material described in Table 6(mass ratio=95:5): Film thickness of 30 nm

Fourth layer: ET-4: Film thickness of 30 nm

TABLE 6 External Light emitting quantum Chroma- Element No. materialefficiency ticity Note Element 4-1  1 1.0 A The present inventionElement 4-2 13 0.8 A The present invention Element 4-3 17 1.0 A Thepresent invention Element 4-4 26 0.5 B The present invention Element 4-532 0.9 A The present invention Element 4-6 34 0.9 A The presentinvention Comparative Comparative 0.4 B Comparative element 4-1 compound1 Example Comparative Comparative 0.3 C Comparative element 4-2 compound2 Example Comparative Comparative 0.9 C Comparative element 4-3 compound3 Example

Example 6

Organic electroluminescent elements 5-1 to 5-5 and comparative elements5-1 to 5-3 were fabricated in the same manner as in Example 2, exceptthat the layer configurations were changed as follows, and evaluationswere carried out in the same manner as in Example 2. The results areshown in Table 7 below. Further, the external quantum efficiency inTable 7 below is expressed as a relative value, taking the value of theorganic electroluminescent element 5-1 using the light emitting material1 as 1.0.

First layer: HAT-CN: Film thickness of 10 nm

Second layer: HT-2: Film thickness of 30 nm

Third layer: H-4 and the light emitting material described in Table 7below (mass ratio=95:5): Film thickness of 30 nm

Fourth layer: ET-2: Film thickness of 30 nm

TABLE 7 External Light emitting quantum Chroma- Element No. materialefficiency ticity Note Element 5-1  1 1.0 A The present inventionElement 5-2 13 0.9 A The present invention Element 5-3 17 0.9 A Thepresent invention Element 5-4 32 0.8 A The present invention Element 5-534 1.0 A The present invention Comparative Comparative 0.3 B Comparativeelement 5-1 compound 1 Example Comparative Comparative Host material CComparative element 5-2 compound 2 emits light Example ComparativeComparative 1.0 C Comparative element 5-3 compound 3 Example

Example 7 Evaluation of Organic Electroluminescent Element (Coating)—Preparation of Light Emitting Layer-Forming Coating Liquids—

The light emitting material 1 (0.1% by mass) and a host material PH-1having the following structure (0.9% by mass) were mixed with methylethyl ketone (98.99% by mass) to obtain a light emitting layer-formingcoating liquid 1.

In the same manner as for the light emitting layer-forming coatingliquid 1, except that the light emitting material 1 was changed to alight emitting material 13 and a light emitting material 34,respectively, in the light emitting layer-forming coating liquid 1,light emitting layer-forming coating liquids 2 and 3 were prepared.

In addition, in the same manner as for the light emitting layer-formingcoating liquids 1 to 3, except that the host material PH-1 was changedto a host material H-2 in the light emitting layer-forming coatingliquids 1 to 3, light emitting layer-forming coating liquids 4 to 6 wereprepared, respectively.

Furthermore, for a Comparative Example, in the same manner as for thelight emitting layer-forming coating liquid 1, except that the lightemitting material 1 was changed to a comparative compound 1 in the lightemitting layer-forming coating liquid 1, a comparative light emittinglayer-forming coating liquid 1 was prepared.

In addition, for a Comparative Example, in the same manner as for thelight emitting layer-forming coating liquid 1, except that the lightemitting material 1 was changed to a comparative compound 1 in the lightemitting layer-forming coating liquid 4, a comparative light emittinglayer-forming coating liquid 2 was prepared.

(Fabrication Procedure for Element) —Fabrication of OrganicElectroluminescent Element 6-1—

ITO was deposited on a 25 mm×25 mm×0.7 mm glass substrate to give athickness of 150 nm, thereby forming a film, which was taken as atransparent supporting substrate. This transparent supporting substratewas etched and washed.

On this ITO glass substrate, 2 parts by mass of PTPDES-2 represented bythe following structural formula (manufactured by Chemipro Kasei Kaisha,Ltd., Tg=205° C.) was dissolved in 98 parts by mass of cyclohexanone forthe electronics industry (manufactured by Kanto Chemical Co., Inc.) andspin-coated (2,000 rpm for 20 seconds) to give a thickness of about 40nm, and then dried at 120° C. for 30 minutes and subjected to anannealing treatment at 160° C. for 10 minutes to form a hole injectinglayer.

The light emitting layer-forming coating liquid 1 was spin-coated on thehole injecting layer (1,300 rpm for 30 seconds) to give a thickness ofabout 40 nm, thereby obtaining a light emitting layer.

Subsequently, BAlq(bis-(2-methyl-8-quinolinolato)-4-(phenylphenolato)-aluminum(III))represented by the following structural formula was formed as anelectron transporting layer on the light emitting layer to give athickness of 40 nm by a vacuum deposition method.

Lithium fluoride (LiF) was formed as an electron injecting layer on anelectron transporting layer to give a thickness of 1 nm by a vacuumdeposition method. Metal aluminum was further deposited to 70 nm thereonto from a cathode.

The laminate thus prepared was put into a glove box purged with an argongas, and then sealed with a sealing can made of stainless steel and anultraviolet-curable adhesive (XNR5516HV, manufactured by Nagase-Chiba,Ltd.) to fabricate an organic electroluminescent element 6-1.

In the same manner as for the organic electroluminescent element 6-1,except that the light emitting layer-forming coating liquid 1 waschanged to light emitting layer-forming coating liquids 2 to 6,respectively, in the organic electroluminescent element 6-1, organicelectroluminescent elements 6-2 to 6-6 were prepared, respectively.

Furthermore, for comparison, in the same manner as for the organicelectroluminescent element 6-1, except that the light emittinglayer-forming coating liquid 1 was changed to comparative light emittinglayer-forming coating liquids 1 and 2, respectively, in the organicelectroluminescent element 6-1, organic electroluminescent elements 6-7and 6-8 were prepared, respectively.

For the organic electroluminescent elements 6-1 to 6-6 and thecomparative elements 6-7 and 6-8 thus prepared, evaluations were carriedout in the same manner as in Example 2. The results are shown in Table 8below. Further, the external quantum efficiency in Table 8 below isshown as a relative value, taking the value of the organicelectroluminescent element 6-1 using the light emitting material 1 asthe same host as 1.0.

TABLE 8 Light Host External emitting mate- quantum Chroma- Element No.material rial efficiency ticity Note Element 6-1  1 PH-1 1.0 A Thepresent invention Element 6-2 13 PH-1 0.9 A The present inventionElement 6-3 34 PH-1 1.0 A The present invention Comparative ComparativePH-1 0.3 B Comparative element 6-7 compound 1 Example Element 6-4 1  H-21.0 A The present invention Element 6-5 13  H-2 0.9 A The presentinvention Element 6-6 34  H-2 1.0 A The present invention ComparativeComparative  H-2 0.3 B Comparative element 6-8 compound 1 Example

From Tables 3 to 8 above, it could be seen that the organicelectroluminescent element of the present invention using theluminescent compound of the present invention has high luminousefficiency and excellent chromaticity.

Meanwhile, it could also be seen that the number of hydrogen atoms ordeuterium atoms in R¹ to R¹⁴ in the general formula (1) is 6, and eachof the comparative elements using the comparative compound 1 describedin JP-A-2005-82702, which has a number below the lower limit of therange in the present invention, has poor external quantum efficiency.

It could be seen that the number of hydrogen atoms or deuterium atoms inR¹ to R¹⁴ in the general formula (1) is 14, and each of the comparativeelements using the comparative compound 2 described in JP-A-05-2143334,which has a number above the upper limit of the range in the presentinvention has poor chromaticity.

It could be seen that the comparative element using the comparativecompound 3 having no skeleton of the general formula (1) has poorchromaticity.

REFERENCE SIGNS LIST

-   -   2: SUBSTRATE    -   3: ANODE    -   4: HOLE INJECTING LAYER    -   5: HOLE TRANSPORTING LAYER    -   6: LIGHT EMITTING LAYER    -   7: HOLE BLOCKING LAYER    -   8: ELECTRON TRANSPORTING LAYER    -   9: CATHODE    -   10: ORGANIC ELECTROLUMINESCENT ELEMENT    -   11: ORGANIC LAYER    -   12: PROTECTIVE LAYER    -   14: ADHESIVE LAYER    -   16: SEALING ENCLOSURE    -   20: LIGHT EMITTING DEVICE    -   30: LIGHT SCATTERING MEMBER    -   31: TRANSPARENT SUBSTRATE    -   30A: LIGHT INCIDENT SURFACE    -   30B: LIGHT OUTPUT SURFACE    -   32: FINE PARTICLES    -   40: ILLUMINATION DEVICE

1. An organic electroluminescent element comprising: a substrate; a pairof electrodes including an anode and a cathode, disposed on thesubstrate; and at least one organic layer including a light emittinglayer, disposed between the electrodes, wherein the light emitting layercontains a luminescent compound represented by the following generalformula (1):

wherein R¹ to R¹⁴ each independently represents a hydrogen atom, adeuterium atom, an alkyl group, an aryl group, a heteroaryl group, afluorine atom, a cyano group, an amino group, an alkoxy group, anaryloxy group, a thio group, or a silyl group, and these may be bondedto each other to form a ring; wherein 8 to 13 groups out of R¹ to R¹⁴each represents a hydrogen atom or a deuterium atom.
 2. The organicelectroluminescent element according to claim 1, wherein at least one ofR¹ to R¹⁴ in the general formula (1) is an electron donatingsubstituent.
 3. The organic electroluminescent element according toclaim 1, wherein at least one of R¹ to R¹⁴ in the general formula (1) isan amino group.
 4. The organic electroluminescent element according toclaim 1, wherein the luminescent compound represented by the generalformula (1) is a luminescent compound represented by the followinggeneral formula (2):

wherein R² to R¹⁴ each independently represents a hydrogen atom, adeuterium atom, an alkyl group, an aryl group, a heteroaryl group, afluorine atom, a cyano group, an amino group, an alkoxy group, anaryloxy group, a thio group, or a silyl group, and these may be bondedto each other to form a ring; R¹⁵ and R¹⁶ each independently representsan alkyl group, an aryl group, a heteroaryl group, or a hydrogen atom,and may be bonded to each other to form a ring or may be bonded to R² orR¹⁴ to form a ring.
 5. The organic electroluminescent element accordingto claim 1, wherein the luminescent compound represented by the generalformula (1) is a luminescent compound represented by the followinggeneral formula (3);

wherein R¹ and R⁴ to R¹⁴ each independently represents a hydrogen atom,a deuterium atom, an alkyl group, an aryl group, a heteroaryl group, afluorine atom, a cyano group, an amino group, an alkoxy group, anaryloxy group, a thio group, or a silyl group, and these may be bondedto each other to form a ring; R³¹ to R³³ each independently representsan alkyl group, an aryl group, a heteroaryl group, or a hydrogen atom,and R³² and R³³ may be bonded to each other to form a ring.
 6. Theorganic electroluminescent element according to claim 1, wherein theluminescent compound represented by the general formula (1) is aluminescent compound represented by the following general formula (4):

wherein R¹, R⁴ to R⁸ and R¹¹ to R¹⁴ each independently represents ahydrogen atom, a deuterium atom, an alkyl group, an aryl group, aheteroaryl group, a fluorine atom, a cyano group, an amino group, analkoxy group, an aryloxy group, a thio group, or a silyl group, andthese may be bonded to each other to form a ring; R³¹ to R³⁶ eachindependently represents an alkyl group, an aryl group, a heteroarylgroup, or a hydrogen atom, R³² and R³³ may be bonded to each other toform a ring, and R³⁵ and R³⁶ may be bonded to each other to form a ring.7. The organic electroluminescent element according to claim 1, whereinthe luminescent compound represented by the general formula (1) is aluminescent compound represented by the following general formula (5):

wherein R² to R⁷ and R⁹ to R¹⁴ each independently represents a hydrogenatom, a deuterium atom, an alkyl group, an aryl group, a heteroarylgroup, a fluorine atom, a cyano group, an amino group, an alkoxy group,an aryloxy group, a thio group, or a silyl group, and these may bebonded to each other to form a ring; R¹⁷ to R²⁰ each independentlyrepresents alkyl group, an aryl group, a heteroaryl group, or a hydrogenatom, and R¹⁷ and R¹⁹ may be bonded to any of R², R¹⁴, or R¹⁸ and any ofR⁷, R⁹, or R²⁰, respectively, to form a ring.
 8. The organicelectroluminescent element according to claim 1, wherein the luminescentcompound represented by the general formula (1) is a luminescentcompound represented by the following general formula (6):

wherein R² to R⁹ and R¹¹ to R¹⁴ each independently represents a hydrogenatom, a deuterium atom, an alkyl group, an aryl group, a heteroarylgroup, a fluorine atom, a cyano group, an amino group, an alkoxy group,an aryloxy group, a thio group, or a silyl group, and these may bebonded to each other to form a ring; R²¹ to R²⁴ each independentlyrepresents alkyl group, an aryl group, a heteroaryl group, or a hydrogenatom, and R²¹ and R²³ may be bonded to any of R², R¹⁴, or R²² and any ofR⁹, R¹¹, or R²⁴, respectively, to form a ring.
 9. The organicelectroluminescent element according to claim 1, wherein the luminescentcompound represented by the general formula (1) is a luminescentcompound represented by the following general formula (7):

wherein R² and R⁴ to R¹⁴ each independently represents a hydrogen atom,a deuterium atom, an alkyl group, an aryl group, a heteroaryl group, afluorine atom, a cyano group, an amino group, an alkoxy group, anaryloxy group, a thio group, or a silyl group, and these may be bondedto each other to form a ring; R²⁵ to R²⁸ each independently representsan alkyl group, an aryl group, a heteroaryl group, or a hydrogen atom,and R²⁵ and R²⁷ may be bonded to any of R², R¹⁴, or R²⁶ and any of R²,R⁴, or R²⁸, respectively, to form a ring.
 10. The organicelectroluminescent element according to claim 1, wherein the lightemitting layer contains an anthracene-based host material.
 11. Theorganic electroluminescent element according to claim 1, wherein thelight emitting layer is formed by a vacuum deposition process.
 12. Theorganic electroluminescent element according to claim 1, wherein thelight emitting layer is formed by a wet process.
 13. A light emittingdevice using the organic electroluminescent element according toclaim
 1. 14. A display device using the organic electroluminescentelement according to.
 15. An illumination device using the organicelectroluminescent element according to-claim
 1. 16. A light emittingmaterial for an organic electroluminescent element, represented by thefollowing general formula (1):

wherein R¹ to R¹⁴ each independently represents a hydrogen atom, adeuterium atom, an alkyl group, an aryl group, a heteroaryl group, afluorine atom, a cyano group, an amino group, an alkoxy group, anaryloxy group, a thio group, or a silyl group, and these may be bondedto each other to form a ring; wherein 8 to 13 groups out of R¹ to R¹⁴each represents a hydrogen atom or a deuterium atom.